Granted, more of a problem on AirBnB due to their complicity in encouraging ever-increasing automation, but there is truly nothing worse than a late check-in lock-out without a safety line or concierge to assist.  

Investing in syndications, done properly, is a lot less risky than described on the BP forums...and also a lot more complicated than discussed on the BP forums.

It is wise to purchase your real estate in an LLC but no need to over complicate the process.

Yes, if you meet all the rules that can get complicated especially for a house hack.

and it's obviously so much more complicated (and expensive!)

Also, due to the complication of figuring it all out, have merely paid the taxes on the land. 

Real estate is not a complicated business. 

This avoids any complications with the 1031 exchange.

if it's already gone to auction, it might be too late. it's a complicated process to try to get the bank to back out of that. and as the other commenter said, all owners have to be totally on board with your plan. not only are most sellers not down for creative financing, but those being foreclosed on are typically even less cooperative (i realize that makes no sense, just how it is), and divorced couples even LESS. i think you're putting the cart before the horse here in looking for a TC. for future deals, you can find a TC in pace morby's fb group. 

Here's my take....you're making things more complicated on every front.1) Buying in Chicago, a very tenant friendly City.2) Bringing in a partner when you don't really need to.3) Buying an expensive property instead of starting off with something more4) Forming an LLC entity right off the bat.Just my $0.02...