Converting your condo into an investment property and transferring it into an LLC is a smart move for liability protection.You’re correct that retitling the property involves Chicago’s transfer tax, which can be substantial.

Seller was not willing to extend contract or accept creative financing options.

Are there other creative options I haven’t considered?

HOA management for a bunch of peripherally involved out-of-town investors is probably a great opportunity pass along overpriced contracts to your local buddies. 

I'm an investor and mortgage broker and have options for loans that go as low as $75,000 and down payments as low as 15%, which makes it easier to stay above $75,000.

Two years ago, this approach would not have been an option.2.

We take your info and we let Lenders battle for the deal offering their best options.

., FTC, HUD and others and the FBI does actually get involved to see if there is a pattern.   

This involves working backward from the final aim to determine the steps.

Hoping to find a local community to get involved with, maybe through Bigger Pockets.