@Jaime Farias I think part of the problem is the learning curve of all the other involved parties.

The best part is you can do it with very little money down using owner occupied loans. 

That is a very critical part. I

My biggest piece of advice is to connect with local chicago real estate investors in person...highly suggest checking out the christmas party on 12/12:  https://www.biggerpockets.com/forums/521/topics/1218823-chic...

You mention a traditional STR PM agreement where the upside is shared by both parties.

They also have a track record of five prior funds which the track record was certified by a third party firm.

I suspect this would happen if various parties were given the ability to ask questions in nearly every application for what this thread touches on - and I have major concerns about integrity (and credibility) issues involved in putting yourself in a position to defend this position if ever challenged. 

As for gray areas in contracts, the courts will almost always find in favor of the party who did NOT write the lease.  

Taking legal action against another party necessarily involves questions of law and can result detrimental legal impacts on him if he files a lawsuit without proper grounds to do so, or where the opposing party may have counter-claims against him.

These studies typically if done by 3rd party would cost $10-$20k but you could also do it on your own.