Ask the manager to explain their process for dealing with maintenance, late rent, evictions, turnover, etc.

If you're unsure about the shut-off process, contacting the city of Chicago for assistance or confirmation is a good idea.Has anyone here used a professional service to winterize their property, and if so, was it worth it?

Were there any surprises or challenges during the bidding process?

Sure- get a full time job, buy a small multifamily, live in one of the units and then repeat that process every year for the next 10 years.

You don't want to serve a notice incorrectly and then go to court for eviction only to find out you did something wrong and now the whole process has to start over again. 

All the investors just say “tap into your equity” but never actually tell you how to get that equity with the loan process. 

I agree with @John UnderwoodPencil out everything (costs, equity, etc.) to create a truly equal partner.When they and you agree on this amount and they pay their part, then you have an equal partner.Of course, in this process, definitely use an attorney.Mike

We are in the process of screening a tenant which of course includes verifying rental history.

I would also ask all contractors about how their draw process works (red flag is: 1/3 up front, 1/3 at half way, and 1/3 at completion.  

I have been considering building a treehouse on a parcel I own as high as I am able with a wrap around deck with 360 degree mountain views as my next project. 
However, I was curious to know if anyone has looked into...