Alternatively i could go for being a real estate broker and try to get experience in actual real estate without putting too much of my own skin in the game.

Since you will likely buy one at a time, work “upstream” to find problems earlier, sift and sort, then work with the prospects that show promise.

Also most townhome developments are part of some sort of HOA and if there is an HOA they will definitely not allow you to form a condo within the bounds of their HOAFeel free to reach out if you have more questions!

I'm specifically interested in "main street" properties with a downstairs retail space, upstairs apartment(s).If you know of anyone with this sort of experience, I'd REALLY appreciate the connection.

They have all sorts of problems now. 

He's still very much in contact and reachable, but my biggest fear is that he will run or file some sort of Bankruptcy.

Sort of same situation but the home was not in that bad of shape. 

This is why you need to do a ton of due diligence on them and make sure they have skin and the game and something to lose.

Which gave me some sort of confidence.

Karma will sort it out.