They seemed good, and looks like they have prior experience managing the building I’m buying (based off the leases that were submitted to me) but way to expensive to what I’m use to … $137 - $184 per door (over 10%) and then $750 per door for the maintenance reserve. 

The fees can be rather exorbitant. 

In your case going to a fifth unit as noted above could actually reduce the value, so I'd be cautious of that since that materially degrades their collateral.

The process involves deeding the property to a land trust and then assigning the beneficial interest of the trust to an LLC for asset protection purposes.2.

Westside of Chicago is tough to make new construction work.It might be a brick veneer around the framing 

We are about 2 years away from pulling the trigger on something.

If it is a high end housing product you may have to use a designer because they have access to some material/finish suppliers that are otherwise unavailable but that tends to only be for the highest end housing deliveries.

To remedy that, the carpets should be ripped up and sealant applied to the subfloor, at minimum.There are also tiles in the smaller upstairs bathroom that are lifting up and creating a safety hazard; putting a rug on top is not a sufficient solution.The house is in a condition that materially interferes with the health of household members.

Second thing would be to work with a contractor, this is great stuff to do since you know building a house, building material costs, and knowledge of right and wrong what to do. 

Fixing and flipping real estate has become one of the hottest ways to build wealth.