@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.

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. 

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

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Chicago urban core burbs, so expect lots of 1950's and 60's construction with galvanized pipes, flat roofs, boilers and outdated electrical.

Tenants, "go into Holiday-mode" and start spending disposable income (and racking up their credit cards) on Thanksgiving feasts & trips, Xmas presents & trips, and finally NYE plans.3) Income Tax Refund checks start being received towards the end of February and corresponding, the rental market starts picking up again as tenants payoff their “Holiday Hangovers".4) Spring Fever starts, sometime in April-May, causing both sales & rental markets to start picking up.

Roof $5000.

Repairs are not factored into the percent rule so you close at 1 percent rule and then you need a new furnace and roof and you won't make money for years on the property.

Maybe roof age or other u/w reasons.

That in the Dean wood area are maybe the only two area in the DC  where the properties have not jump through the roof.

My repair costs are near zero because I do all work myself, from roofing to furnaces to sewers.