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. 

A few of mine include:Draining outside hoses, and bowling out any irrigationTesting sump pump and removing/draining any hose extensionsCleaning out gutters to avoid ice damsThermostat upgrade to a smart thermostat to conserve energyFurnace cleaning & check upFriendly reminder to tenants on snow removal responsibility :) What's on your list?

Also, I have been listening to the podcasts here and there but of course I think that's a little advance since I'm not entirely sure yet what they're talking about, however, they really make me excited for some reason and really pumps me every time I listen to them.

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).