Thanks everyone, appreciate the suggestions, very helpful! 

Although your suggestion has been considered, it'll cost a lot less to renovate & upgrade it than starting over elsewhere. 

Based on your description I'd suggest starting by reading the book: Who Not How https://a.co/d/eLZv7lFI think we all start off more DIY and getting our hands dirty.

I've joined the AOA and reviewed their lease agreement, but it seems like overkill, though I do like some of their addendums (bedbugs, plumbing etc).

With lad cost and cost of construction I have been having a hard time doing that and that is why now I am looking for different options and suggestions.

I suggest buying a brick building if you go that route- was in a similar situation in 2018 and bought a wood building but wish i had gone with brickstraight up chicago real estate investor podcast is a great way to learn what others are doing all over the city

Any advice / suggestions is greatly appreciated!! 

Any suggestion on the best way to look up historical comp value of a home?

@Anthony DelVecchio I would suggest having some amount of money saved in reserves for just the type of emergency repairs you have mentioned before buying your first house/property.

My suggestion would be to pick one strategy because they all work over time (direct mail, PPC, driving for dollars, cold calling, texting, billboards, radio), and don't stop that until you have consistent deal flow.Also, I highly suggest finding someone who is already wholesaling and get on their team!