I'm in Chicagoland, but south burbs.I read and researched a lot, but ultimately I got started by following the steps in this book: The Weekend Millionaire's Secrets to Investing in Real Estate: How to Become Wealthy in Your Spare Time https://a.co/d/gLYA4SjThey give you the step by step.

But, ultimately, you're right - strong appreciation can justify a cashflow negative investment in some cases. 

So I'd recommend thinking about who you want in the property and then determining the bed configurations and numberthank you so much, great things to think about: i hear others echo your sentiment not to count the sleeper sofa as a bed as much as a 'bonus' if people ask, so i appreciate this insight. i thought it might be okay, as it's memory foam with a topper, but ultimately i agree that it's not where i'd want to sleep.

And at the end of the day, I would assume these are the types of investors you want to ultimately service, since they are more likely to be actual buyers and not just dreamers.

there are tools like STR insights, bnbcalc and airdna that can help identify a good market but ultimately a lot of your success will come down to location and how well the property is managed.

Here are a few I recommend: "Rich Dad, Poor Dad" by Roberto Kiyosaki; "Set for Life" by Scott Trench; "The Unofficial Guide to Real Estate Investing" by Spencer; "The BiggerPockets Ultimate Beginners Guide" found here on BP; "The Book on Rental Property Investing" by Brandon Tuner.

Here are a few I recommend: "Rich Dad, Poor Dad" by Roberto Kiyosaki; "Set for Life" by Scott Trench; "The Unofficial Guide to Real Estate Investing" by Spencer; "The BiggerPockets Ultimate Beginners Guide" found here on BP; "The Book on Rental Property Investing" by Brandon Tuner.

Now we just have to focus on scaling over time to meet your ultimate cash flow goals. 

.: BiggerPockets Ultimate Beginners Guide (free) and The Book On Rental Property Investing by Brandon Turner or The Unofficial Guide to Real Estate Investing by Spencer Strauss (although it's no longer in print, you can find used copies).

My ultimate question is if, in a contract for deed sale, the property tax steps up.