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...

Most people can do their books themselves if the business is not too complicated, but is that the best use of your time.

Also, split AC sounds complicated to the folks who have visited the property so far.

FLLC2 also owns WLLC.Sorry for what may seem complicated.