I plan to short and/or mid term rent it out and the numbers look reasonable without flood insurance. 

It's a short term loan with no PPP that offers money to close on an acquisition and also provide escrowed rehab funds for the work needed.

the short answer is... the deal has to work based on all of the findings and factors. 

I would start with your short and long-term goals.

Think about your target strategies, like short-term or long-term rentals, and whether you're looking for financing options to expand your portfolio.

You usually need to lock up the deal and get a lot of those things done during the process.Buying near your son's college would be a great idea if you plan on having him house hack there and manage or learn or use one unit as short-term or mid-term for when you visit. 

We like residential and want to do more long and short term rental but are becoming more and more interested in commercial like industrial or office.

Great tools that get updated regularly.I am on the lending side of things and would be happy to hop on a call with you anytime to discuss financial strategies and help answer any questions you may have about nearly any loan product available to help you on your journey, even if they are not products my capital partners offer.I just gave a list of my recommended reading to another poster, but will happily post it here again.Personally, my short list of books to explore:Set For Life by @Scott TrenchRich Dad Poor Dad by Robert KiyosakiABCs of Real Estate Investing by Ken McElroyABCs of Buying Rental Property by Ken McElroyLoopholes of Real Estate by Garrett Sutton, EsqTax-Free Wealth by Tom Wheelwright, CPAThe Power of Zero by David McKnightREIT Investing for Beginners by Lawrence SmithWhat Would the Rockefellers Do?

Hey everyone, Has anyone done short term rentals in Chicago.

In short, excellent experience and no issues with them.