I've done it with credit card payments on vacation rentals, won every time, and the money was returned to me.I will bet this is a tenant with a lower credit score.

You are betting on them to build the condos to the standard they are promising you! 

Maybe the best bet is a rental refi on one of the two existing properties to be able to get a new home all cash?

Here's another key...we usually want to see that someone has done similar projects in the past...or at least projects of progressively increasing complexity. 

We have a small 3 bd 1 bath home that is  in the path of progress.

There are definitely situations where selling to a wholesaler is someone's bets option, but they're the exception, not the rule.

I'd be willing to bet most of the tenant problems people post on BP about are when they make an exception to their screening criteria. 

We love intown living and our ideal situation is a house with some character in a diverse neighborhood with community gardens, BeltLine, etc.We have heard and seen an opportunity on the Westside (Grove Park, West End, Adair Park, Capitol View / Perkerson Park, and some streets in Mozley Park) with all of the exciting developments that are planned or in progress.

I bet you can find your answers in the city of Chicago tenant's law and regulations@Carlos Valencia @Albert Bui

Again, I'm not local so I'm just taking every cost and push-back on progress at face value.It's $80 per door, per year, plus the one time inspection fee, which I was thinking was $180, but don't recall exactly right now.