If you come to me and say you super handy ready to take on a major renovation my answer will be different compared to if you come to me saying you need turnkey and 30 minute commute to NYC.  

@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?

This is different than being a certificate holder & the distinction between certificate holder and additional insured is significant3.

     * 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.

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

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

This allows you to compare prices quickly.

Then compare that with your normal 30-year fixed.