That said, we want to avoid tunnel vision, and want to put this out to the larger community to see what other locations you have had experiences in, and their pros/cons compared to a place like Cleveland.

If the cat house is in the flood zone, but the larger house is not, after demo a buyer would no longer need to carry Flood insurance per the loan requirements.  

I'm interested in moving up to larger deals myself going forward.

All those who make money off selling hope will tell you to "jump in" because they have not dog in the hunt and their money is not at risk.

Couple things to keep in mind... the down payment requirements are larger (around 15-25%) on DSCR loans.

What did you learn during this process that will allow you to make a much larger profit on the next one?

In the larger public square, like here, we still engage the issues. 

For example, maybe you have capital gains from a stock sale and you are holding a dog stock that lost money.

Reasons for moving to Single Family are two dogs and a Baby on the way!

Dog outside yard, vehicle blocking, offsite dumping, dumpster diving...?