I'd like to pick a good platform and keep everything under one roof - not need multiple tools. 

External is usually where they want to approve the color of the house, types of materials, roofing, landscaping, driveway condition, etc.

Roof: 7-8kHVAC: 4-5kWell Filters: $0 -3kStain: 4-5kFurniture (Entire house): 8-10kAppliances (stove/fridge/dishwasher): 3KI think I've covered all the big ones. 

The building stock is like all the other Chicago urban core burbs, so expect lots of 1950's and 60's construction with galvanized pipes, flat roofs, boilers and outdated electrical.

@Kelsey Vander Meulen unless you have a great team lined up, especially someone who can address a burst pipe or damaged roof late night or on a Sunday, hire management.

And most will be able to pay the taxes when they come due, and put on a new roof, and put on a new coat of paint.As well as replace the carpets, cut the grass on a regular basis, replace the windows, reseal the chimneys when the liners crack, etc..It's unlikely that that these homes will fall into the slum category in 10 years or so, and make the asset underlying the loan virtually worthless.Or just vanish when the place starts to fall apart too much, due to no down-payment (no skin in the game 100% loans).Said the lawmakers who approved this.

., roof replacement, appliance upgrades) as a reserve.3.

Where is it leaking, roof composition, pitch, etc? 

Roof $5000.

Maybe roof age or other u/w reasons.