Chicago Real Estate Investing & Real Estate Financial Planning™ Podcast

James Orr

Learn all about investing in real estate in Chicago, Illinois with a combination of real estate financial planning and modeling with numbers specific to Chicago plus syndicated, more generalized recordings of live and pre-recorded real estate investing classes (not all specific to Chicago). read less
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Improving Cash Flow on Rental Properties by Improving the Property
6d ago
Improving Cash Flow on Rental Properties by Improving the Property
Improving Cash Flow on Rental Properties by Improving the Property When real estate prices, mortgage interest rates, and rent rates are high, it can be more challenging to generate great cash flow from a rental property. However, it is also more important than ever to do everything in your power to maximize cash flow. There are 88 strategies for improving cash flow on rental properties, with some significant ones that you can apply by making improvements to your rental property. This mini-class covers the cash flow improving strategies that you may make by improving the property. Check out the video from this class here: Improving Cash Flow on Rental Properties by Improving the Property - Video In this class, James discusses: The 7 stages to improve cash flow on rental propertiesSubdividing propertiesUpgrading the propertyAdding solar to the propertyProviding furnished rentalsConverting the propertyCharging improvement rent for tenant-requested improvementsHow to calculate the ROI on making improvementsPlus much more... Free Real Estate Deal Analysis Spreadsheet: Download a copy of the newest version of The World's Greatest Real Estate Deal Analysis Spreadsheet™ by going to:https://RealEstateFinancialPlanner.com/spreadsheetImprove Cash Flow: Book a consultation to improve cash flow using our proprietary 88 cash flow improving strategies.Real Estate Agent & Lender Collaborators: Interested in collaborating with us on the Chicago real estate investor podcast? Book a free consultation to discuss.
Financing Tips When Writing an Offer to Buy a Rental
Nov 17 2023
Financing Tips When Writing an Offer to Buy a Rental
Financing Tips When Writing an Offer to Buy a Rental So, you understand financing for buying your next property, and you're ready to go out in search of a property to buy. There are a few financing-related tips that might help set you up for success, improve the odds of getting your offer accepted, getting the best price and terms on your offer, and make your life easier. That's what we will discuss in this mini-class. Check out the video from this class here: Financing Tips When Writing an Offer to Buy a Rental - Video In this class, James discusses: What you should have done (and in hand) before you go look at properties?What you absolutely need before you write an offer on a rental property?What you can do with your lendeer to give yourself that extra edge when writing an offer to buy a property?Why you should get a pre-approval letter with your MAXIMUM loan amount from your lender... even if you never intend to ever go close to your maximum.Why waiting until the last minute can make you miss out on the very best dealsThe pros and cons of using the max or the offer price on your pre-approval letterPlus much more... Free Real Estate Deal Analysis Spreadsheet: Download a copy of the newest version of The World's Greatest Real Estate Deal Analysis Spreadsheet™ by going to:https://RealEstateFinancialPlanner.com/spreadsheetImprove Cash Flow: Book a consultation to improve cash flow using our proprietary 88 cash flow improving strategies.Real Estate Agent & Lender Collaborators: Interested in collaborating with us on the Chicago real estate investor podcast? Book a free consultation to discuss.
Is It Better to Sell Properties to Invest in Stocks If That Means Financial Independece When Nomading™?
Nov 10 2023
Is It Better to Sell Properties to Invest in Stocks If That Means Financial Independece When Nomading™?
Sometimes buying rental properties is merely a means to an end: financial independence. Some folks don't want to hold onto their rental properties, manage them, or deal with the business of owning them when they achieve financial independence. Instead, they may prefer to have their money more passively invested in stocks. Can a real estate investor buy properties and hold onto them until they can sell off all the rentals, pay all their expenses of the sale—including closing costs, capital gains taxes, depreciation recapture taxes, and real estate commissions—then take the proceeds and invest in the stock market utilizing a safe withdrawal rate? And is that a faster approach to achieving financial independence than trying to get your properties to the point where they're cash flowing enough to support you without working? In this mini-class, James will look at Nomading™ versus Nomading™ but being willing to sell off all your rental properties if doing so can make you financially independent and allow you to invest in stocks using a safe withdrawal rate. Check out the video and interactive charts from this class here: https://RealEstateFinancialPlanner.com/model/nomad-selling-all-rentals-fi-swr/ Or, see Chicago specific, detailed analysis of a variety of strategies here: https://RealEstateFinancialPlanner.com/model/IL/Chicago/ Free Real Estate Deal Analysis Spreadsheet: Download a copy of the newest version of The World's Greatest Real Estate Deal Analysis Spreadsheet™ by going to:https://RealEstateFinancialPlanner.com/spreadsheetImprove Cash Flow: Book a consultation to improve cash flow using our proprietary 88 cash flow improving strategies.Real Estate Agent & Lender Collaborators: Interested in collaborating with us on the Chicago real estate investor podcast? Book a free consultation to discuss.
Tips for Getting Mortgage Quotes from Lenders
Nov 3 2023
Tips for Getting Mortgage Quotes from Lenders
Tips for Getting Mortgage Quotes from Lenders If you choose a random lender, you'll have a random chance of closing with financing. And in many markets, if your lender fails to perform, you as the buyer are in default (since your lender is not a party to the contract). Wouldn't you rather have more certainty that your lender will perform and that you select a lender that will give you great service, with reasonable fees, and a great mortgage interest rate? Yes, it seems like a very reasonable expectation. In this mini-class, James will go over tips for selecting and getting mortgage quotes from lenders. Check out the video from this class here: Tips for Getting Mortgage Quotes from Lenders - Video In this class, James discusses: The best sources for finding a great lenderWhy choosing a random lender gives you a random chance of successfully closing on your propertyWho is responsible if the lender you choose does not perform?Tips for calling lendersShould you have your lender pull your credit report?Why you should you call all your prospective lenders on the same dayLender questions to askQuestions to ask about your lenders fees and their teamGetting references from your lenderPlus much more... Free Real Estate Deal Analysis Spreadsheet: Download a copy of the newest version of The World's Greatest Real Estate Deal Analysis Spreadsheet™ by going to:https://RealEstateFinancialPlanner.com/spreadsheetImprove Cash Flow: Book a consultation to improve cash flow using our proprietary 88 cash flow improving strategies.Real Estate Agent & Lender Collaborators: Interested in collaborating with us on the Chicago real estate investor podcast? Book a free consultation to discuss.
Ways to Speed Up Achieving Financial Independence
Oct 30 2023
Ways to Speed Up Achieving Financial Independence
How can you speed up your journey to financial independence (FI)? In this special class, James will go over a brand-new spreadsheet and walk you through all the different ways to speed up your achievement of financial independence. James covers the following in this class: What is financial independence?How is financial independence defined mathematically? How do you know if you're financially independent?A brief discussion of pensions, annuities, and social security and why you may prefer to focus elsewhereAn introduction to the new Financial Independence Asset Allocation and Cash Flows Engine™ spreadsheet Speeding up FI via job incomeSpeeding up FI via propertiesSpeeding up FI via business profitsAn introduction to Safe Withdrawal RatesSpeeding up FI via invested assets (and a SWR)Speeding up FI with annuitiesBesides earning more money and reducing expenses, what are the strategies for achieving FI faster?Sources of money to invest... and allocating that money to speed up FIInvesting or reinvesting in what to speed up FI?The three primary groups of strategies to improve speed to FI: increase savings, increase returns, and reallocate assets.All the strategies for increasing savingsAll the strategies for increasing returnsA discussion of Return on Equity and why it matters when you're trying to speed up your achievement of financial independenceAll the strategies based on reallocating assetsRisk versus speed - a tricky tradeAnd much more... Free Real Estate Deal Analysis Spreadsheet: Download a copy of the newest version of The World's Greatest Real Estate Deal Analysis Spreadsheet™ by going to:https://RealEstateFinancialPlanner.com/spreadsheetImprove Cash Flow: Book a consultation to improve cash flow using our proprietary 88 cash flow improving strategies.Real Estate Agent & Lender Collaborators: Interested in collaborating with us on the Chicago real estate investor podcast? Book a free consultation to discuss.
Preparing to Get Mortgages
Oct 27 2023
Preparing to Get Mortgages
Preparing to Get Mortgages So, you’ve decided to invest in real estate and know that you’ll need a mortgage to buy property. There are some things you should do BEFORE you apply for your mortgage. You should be thinking about these things ideally for multiple years before you try to get a mortgage. In this mini-class, we will discuss the preparation you should do before getting a mortgage and how to make the process faster, better, and easier, especially if you plan to buy more than one property. Check out the video from this class here: Preparing to Get Mortgages - Video In this class, James discusses: Knowing your qualification requirements from your lenderGetting a loan when you're self-employedDon't be penny-wise, pound-foolishKnowing and improving your credit score (one way to maximize cash flow)Understanding Debt-To-Income and using it to your advantage to maximize cash flowSaving money preparing to get mortgage (and uses of that money to make sure you optimize cash flow)A list of often requested document when applying for a mortgageOrganizing your files to be prepared for applyingPlus much more... Free Real Estate Deal Analysis Spreadsheet: Download a copy of the newest version of The World's Greatest Real Estate Deal Analysis Spreadsheet™ by going to:https://RealEstateFinancialPlanner.com/spreadsheetImprove Cash Flow: Book a consultation to improve cash flow using our proprietary 88 cash flow improving strategies.Real Estate Agent & Lender Collaborators: Interested in collaborating with us on the Chicago real estate investor podcast? Book a free consultation to discuss.
The Return on Investment on Extra Down Payments
Oct 13 2023
The Return on Investment on Extra Down Payments
The Return on Investment on Extra Down Payments You’re buying a rental property. You have more than you need for a down payment, closing costs and reserves. One option you’re considering is putting more down. Putting more down will often improve cash flow and Cash on Cash Return on Investment. The dollar amount of returns from Appreciation and Depreciation remain unchanged but, it can also lower your overall return on investment from Appreciation and Depreciation because your investment amount has changed. And putting more down changes how much debt you pay down and the amount you invested lowering your return on investment from debt paydown. In this mini-class, James will look at how putting more down changes your return on investment so you can make an educated decision as to whether it makes sense or not to put more down and see improved cash flow. Check out the video from this class here: The Return on Investment on Extra Down Payments - Video In this class, James discusses: James Orr's Return Quadrants™: Return in Dollars Quadrant™, Return on Investment Quadrant™ and Return on Equity Quadrant™ Loan Comparison SpreadsheetThe returns in dollars for Nomad™ with 5% downThe return on investment for Nomad with 5% downThe returns and ROI for 15% downHow 5% Nomad™ compares to 15% down and the return on the extra down paymentSimilar comparisons for 20%, 25%, 30% and 40% down payment options Cash on Cash Return on Investment approaches Cap Rate Plus much more... Free Real Estate Deal Analysis Spreadsheet: Download a copy of the newest version of The World's Greatest Real Estate Deal Analysis Spreadsheet™ by going to:https://RealEstateFinancialPlanner.com/spreadsheetImprove Cash Flow: Book a consultation to improve cash flow using our proprietary 88 cash flow improving strategies.Real Estate Agent & Lender Collaborators: Interested in collaborating with us on the Chicago real estate investor podcast? Book a free consultation to discuss.
Is It Better to Pay Off Your Owner-Occupant Mortgage When Nomading?
Oct 6 2023
Is It Better to Pay Off Your Owner-Occupant Mortgage When Nomading?
Most real estate investors consider themselves financially independent when the income from all of their investments exceeds their personal expenses. To achieve this, they need net positive cash flow from all rental properties after all expenses, any income generated from stocks, bonds, or other investments times a safe withdrawal rate, and any social security, pensions or annuities. On the expense side, they need to consider all personal expenses, such as food, taxes, insurance, entertainment, healthcare, and housing. If they have a mortgage on their personal residence, that would include their mortgage payment. However, paying off the mortgage effectively reduces the amount of income needed to cover expenses by the amount of the mortgage payment that no longer exists. If you have extra money invested in stocks, bonds, or other assets and could pay off your mortgage to achieve financial independence, it may be worth considering. This mini-class will explore the impact of paying off your owner-occupant mortgage and its effect on achieving financial independence faster than the traditional Nomad™ strategy. We will also examine how this decision could impact your net worth and compare the risks to the traditional Nomad™ strategy. Check out the video and interactive charts from this class here: https://RealEstateFinancialPlanner.com/model/nomad-or-pay-off-oo-fi/ Or, see Chicago specific, detailed analysis of a variety of strategies here: https://RealEstateFinancialPlanner.com/model/IL/Chicago/ Free Real Estate Deal Analysis Spreadsheet: Download a copy of the newest version of The World's Greatest Real Estate Deal Analysis Spreadsheet™ by going to:https://RealEstateFinancialPlanner.com/spreadsheetImprove Cash Flow: Book a consultation to improve cash flow using our proprietary 88 cash flow improving strategies.Real Estate Agent & Lender Collaborators: Interested in collaborating with us on the Chicago real estate investor podcast? Book a free consultation to discuss.
Should I Put 15% or 20% Down When Buying a Rental Property?
Sep 29 2023
Should I Put 15% or 20% Down When Buying a Rental Property?
Should I Put 15% or 20% Down When Buying a Rental Property? In a real estate market that has seen significant increases in property prices and rapidly rising mortgage interest rates, it can be harder than ever to obtain decent cash flow. However, many real estate investors are tempted to minimize their down payments to optimize their overall returns by investing as little as possible in the deal. A debate looms regarding whether a 15% or 20% down payment is preferable when purchasing an investment property. In this mini-class, James will guide you through a method for approaching this classic problem and provide some mathematical reasoning to help you reach a rational solution once and for all. Check out the video from this class here: Should I Put 15% or 20% Down When Buying a Rental Property? - Video In this class, James discusses: Comparing various loan programsGetting mortgage interest rates and private mortgage insurance from your lenderHow to compare two differnet loan programs... using the example of 15% down versus 20% down when buying a rentalCalculating the return on the extra down payment for yourself on your own deals Download the Loan Comparison SpreadsheetPlus much more... Free Real Estate Deal Analysis Spreadsheet: Download a copy of the newest version of The World's Greatest Real Estate Deal Analysis Spreadsheet™ by going to:https://RealEstateFinancialPlanner.com/spreadsheetImprove Cash Flow: Book a consultation to improve cash flow using our proprietary 88 cash flow improving strategies.Real Estate Agent & Lender Collaborators: Interested in collaborating with us on the Chicago real estate investor podcast? Book a free consultation to discuss.
Loan Comparison Spreadsheet for Real Estate Investors
Sep 22 2023
Loan Comparison Spreadsheet for Real Estate Investors
Loan Comparison Spreadsheet for Real Estate Investors Sometimes it can be helpful to compare various loan programs and options simultaneously. For example, it could be useful to compare the monthly payment differences between various "nothing down," "low down," and full-size down payment options when buying a rental property. Visually seeing a chart comparing the monthly payments of your choices of loans can assist you in making better decisions. If you had a spreadsheet to easily compare a variety of loan programs at the same time, it would be even more helpful. In this mini-class, James will share with you a loan comparison spreadsheet that allows you to easily compare all of the most common traditional financing options for real estate investors. Check out the video from this class here: Loan Comparison Spreadsheet for Real Estate Investors - Video In this class, James discusses: Comparing various loan programsGetting mortgage interest rates and private mortgage insurance from your lenderOptimizing cash flow by minimizing monthly loan expensesCommon loan differences between owner-occupant loans for investors utilizing Nomad™ and House Hacker strategiesCommon loan differences for non-owner-occupant loansDownload the Loan Comparison SpreadsheetPlus much more... Free Real Estate Deal Analysis Spreadsheet: Download a copy of the newest version of The World's Greatest Real Estate Deal Analysis Spreadsheet™ by going to:https://RealEstateFinancialPlanner.com/spreadsheetImprove Cash Flow: Book a consultation to improve cash flow using our proprietary 88 cash flow improving strategies.Real Estate Agent & Lender Collaborators: Interested in collaborating with us on the Chicago real estate investor podcast? Book a free consultation to discuss.
Buying Down Mortgage Interest Rates for Real Estate Investors
Sep 15 2023
Buying Down Mortgage Interest Rates for Real Estate Investors
Buying Down Mortgage Interest Rates for Real Estate Investors There are several ways to improve cash flow on your rental properties. One option is to put more money down to reduce the amount you borrow. In some cases, this can also improve your interest rate by lowering your overall loan-to-value. However, when comparing putting more money down to buying down the mortgage interest rate, it is usually better to buy down the interest rate for any reasonable holding period. This is true from both a return on investment and improved cash flow perspective. Learn more about buying down your interest rate in this mini-class. Check out the video from this class here: Buying Down Mortgage Interest Rates for Real Estate Investors - Video In this class, James discusses: Buying down mortgage interest rates when buying a rental propertyImproving cash flow by buying down your rateYou can choose your interest rate by how much you're willing to pay or receive as a credit toward closing costsRate changes for the life of the loanWhat's a point and how do they work?What's par rate and why it is critically important to seek clarity from your lender when they quote you a rate?What can you do with extra money when buying a rental property?Comparing more down payment to buying down your interest rateRequesting a buy down table from your lender (and what they look like)Plugging numbers into the buy down spreadsheetLooking at the cost difference when buying down your rates to various levelsSelecting where to buy down toSimple and compound return on investment calculations done for youPutting more down improves cash flow in 3 important waysComparing more down payment to buying down interest rates (not just cash flow... cash flow and equity)Temporary solution to buying down rate or pre-paying PMIDownload the Mortgage Buy Down SpreadsheetPlus much more... Free Real Estate Deal Analysis Spreadsheet: Download a copy of the newest version of The World's Greatest Real Estate Deal Analysis Spreadsheet™ by going to:https://RealEstateFinancialPlanner.com/spreadsheetImprove Cash Flow: Book a consultation to improve cash flow using our proprietary 88 cash flow improving strategies.Real Estate Agent & Lender Collaborators: Interested in collaborating with us on the Chicago real estate investor podcast? Book a free consultation to discuss.
Other Financing Options for Real Estate Investors
Sep 8 2023
Other Financing Options for Real Estate Investors
Other Financing Options for Real Estate Investors In the last several classes, we covered a variety of traditional financing options, including nothing-down financing, low down payment financing, conventional financing, and portfolio loans. These options represent the overwhelming majority of financing options used when purchasing properties. However, there are a handful of financing options that are used infrequently, but it's still important to be aware of them. In this mini-class, we will discuss these other financing options, including private money, hard money, utilizing partners for financing, home equity lines of credit, owner financing, life insurance, self-directed retirement accounts, subject to and wrap financing, lease-options/lease-purchases, and foregoing financing to pay cash. Check out the video from this class here: Other Financing Options for Real Estate Investors - Video In this class, James discusses: Primary financing types that make up 90%+ of all loansCreative financing: owner financing, wrap financing, lease-options/lease-purhcases, loan assumption, subject to, etcPrivate financingHard moneyLine of credit (HELOCs)Buying properties for cashPartnerships (utilizing all the other strategies)Portfolio loansLife insuranceSelf-directed retirement accountsPlus much more... Free Real Estate Deal Analysis Spreadsheet: Download a copy of the newest version of The World's Greatest Real Estate Deal Analysis Spreadsheet™ by going to:https://RealEstateFinancialPlanner.com/spreadsheetImprove Cash Flow: Book a consultation to improve cash flow using our proprietary 88 cash flow improving strategies.Real Estate Agent & Lender Collaborators: Interested in collaborating with us on the Chicago real estate investor podcast? Book a free consultation to discuss.
Is it Better to Nomad™ or Buy Rentals All Cash?
Sep 1 2023
Is it Better to Nomad™ or Buy Rentals All Cash?
Prices have gone up rapidly in the last few years. And, interest rates are much higher. And even though rents are up, they’re not up enough to counteract the much higher prices and much higher interest rates. That makes it harder to achieve good cash flow with a reasonable down payment. One way to overcome the impact of higher interest rates is to not use loans to buy rental properties. In this comparison mini-class James will compare the Nomad™ real estate investing strategy to taking the significantly longer extra time to save up and buy rental properties for cash. With the Nomad™ strategy, James will have you put 5% down and buy an owner-occupant property that you live in for at least a year until you’ve saved up the next 5% down payment plus closing costs and reserves. Then, buy another 5% down payment owner-occupant property and move into the new property. Convert the previous property to a rental. Repeat this process until you’ve acquired 10 properties total—9 of them rental properties you purchased with 5% down payments. When buying properties for cash, you’ll still buy your first property with 5% down payment and move in. But, after that, you’ll take the significantly longer time to save up 100% to buy a rental property all cash. And, free and clear properties without loans have much, much better cash flow than properties financing with 5% down. But, it takes a lot longer to save up to buy the first property. Keep saving until you buy up to 9 rentals all cash. Which strategy will get you to financial independence fastest? Which will get you the highest net worth? Which is riskiest? We will analyze this comparison for 305 US cities. Check out the video and interactive charts from this class here: https://RealEstateFinancialPlanner.com/model/nomad-versus-1-oo-then-9-all-cash/ Or, see Chicago specific, detailed analysis of a variety of strategies here: https://RealEstateFinancialPlanner.com/model/IL/Chicago/ Free Real Estate Deal Analysis Spreadsheet: Download a copy of the newest version of The World's Greatest Real Estate Deal Analysis Spreadsheet™ by going to:https://RealEstateFinancialPlanner.com/spreadsheetImprove Cash Flow: Book a consultation to improve cash flow using our proprietary 88 cash flow improving strategies.Real Estate Agent & Lender Collaborators: Interested in collaborating with us on the Chicago real estate investor podcast? Book a free consultation to discuss.
The Importance of Loan Planning for Real Estate Investors
Aug 25 2023
The Importance of Loan Planning for Real Estate Investors
The Importance of Loan Planning for Real Estate Investors Real estate investing is a little like the game of Chess. You can play the game with an elementary understanding of the basic rules. But, you soon learn that just knowing how the pieces move about the board are the table stakes for being able to sit at the game board. If you want to do well, you need to start thinking about the consequences of your actions. And, not just the consequences of your actions for the immediate next move, but the consequences for moves multiple turns into the future. The same applies to real estate investing... you need to be thinking not just about the deal analysis and loan of the property right in front of you; that’s table stakes. You need to be thinking about what the consequences are for that property far off into the future and, if you’re good, for multiple properties and multiple loans into the future. That’s why loan planning is so important and why we’ll cover it in detail in this mini-class. Check out the video from this class here: The Importance of Loan Planning for Real Estate Investors - Video In this class, James discusses: The 10 loan limit from Fannie Mae and Freddie Mac for purchasing non-owner-occupant investment propertiesWhy are these loans important to real estate investorsWhat do you use after you reach the limit?Why is it important to optimize these 10 loan spots?What are some exceptions to the 10 loan rule?A strategy to double your loan spotsThe Nomad™ preferred loan planPlus much more... Free Real Estate Deal Analysis Spreadsheet: Download a copy of the newest version of The World's Greatest Real Estate Deal Analysis Spreadsheet™ by going to:https://RealEstateFinancialPlanner.com/spreadsheetImprove Cash Flow: Book a consultation to improve cash flow using our proprietary 88 cash flow improving strategies.Real Estate Agent & Lender Collaborators: Interested in collaborating with us on the Chicago real estate investor podcast? Book a free consultation to discuss.