I’m in Michigan and I’m not sure of the LLC creation 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.

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?

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

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

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

Were there any surprises or challenges during the bidding process?

The featured agent program is still in its infancy and we are constantly improving our processes to make both the BiggerPockets investors and featured agents as successful as we can.

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

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.