@Evan SwansonIt can helpful to have some key metrics to help filter out potential cities.

Require fire extinguishers in the kitchen, laundry room,  water heater room.

I have asked for all these in these past only to be refused by the company>Details of work order/repair request submitted by tenantsDetails of before and after pictures for certain major repairs such as drywallDetails of invoice breakdown such as parts, labor or hoursThe company would not consult with me on any repairs except once they checked with me for a $1700 water heater change out.These are some of the recent ledger entrees: Do these seem reasonable for Milwaukee area.

Should I request a special type of water penetration inspection?

what is the water piping, drains, electric, sewer and heating system condition?

Electric, cable/wi-fi, water etc to make it make more sense and also avoid a more aggressive contract.

There are brokers that do have good relationships with all the agency lenders and can help you navigate the waters. 

You don't want water getting behind the shower walls and rotting wood.  

By winterizing I actually meant draining the water supply lines and filling them with antifreeze.. vs redoing insulation in a crawl space.

It was almost sold, but one week ago, buyer's agent found our house full of water, because of toilet tank leaking during almost 10 days( we live already different state, and our agent worked on listing and selling our home).