@Jamie ParkerAppreciate the effort and plan you are taking - it part of every plan is to re evaluate to move forwardHow much time have you spent compared to how much have you made?

I mean just look at the cheapest rental properties in your area or our area .. and compare them with mid range or higher end ... which would you prefer to own and which do you think are more safe and consistent

     * House is a 2699 sq/ft Single Family Residence| 3 beds, 3 bathroom | Built in 1956 | NO HOA     * There is a chance I could pay only interests so I can start saving some cash for the incoming maintenance and annual payment equivalent to the 12 monthly payments (~$5,029.77 per year during the balloon period)The advantages I can identify in this deal for me are:* Lower interest compared with traditional loans* Lower down payment compared with the ones compared for traditional loans* House is technically ready to be rented (waiting for the inspection) * Forecast - 3 yr growth (appreciation) is expected to be 8.1 % (Bigger Pockets)The disadvantages I can identify: * I am still vulnerable to foreclosure if sellers don't make mortgage payments to the bank.* Refinancing issues at the end of the Balloon Payment?

I STR it for 15-20K a month in the summer, and was offering it for rent for $2100 a month in the winter (lower than any comparable houses), and was getting tire kickers at that price. 

There are a lot of variables to consider so it's impossible to say if investing in one of those other markets would have been "better".However, I think you could make a stronger case that you have been (or would be) more successful with your real estate investing in Chicago compared to other markets.

It would be great to compare notes - how do you feel about expanding your search radius or even considering new-build opportunities further inland?

A HYSA is a type of savings account that offers higher interest compared to traditional savings accounts!

This allows you to compare prices quickly.

Then compare that with your normal 30-year fixed.

Ponts can be built into your rate as well so compare notes with more than one lender/bank.