I've done this before and made it a small daily penalty/bonus amount. 

I currently own and self-manage two STRs in Maine and should be closing on a small 'cabin campground' with 10 cabins nearby that will also be operated as STRs. 

Most amounts are too small for the hassle, and again, that becomes litigation, not simply an audit.Creative finance buyers, I do not believe it's a winning argument to the IRS to say that you bought the property, didn't make the payments and you took the write offs anyway.

He is a realtor that I previously purchased a small portfolio from and therefore had a good professional relationship.

The garage does have electric ran with a small meter base.

Quote from @Richard Kim: I'm a fairly new small time out of state investor who owns a couple multi-family properties in Cleveland.

Given they are going to damage the walls while moving anyway it eliminates their need to touch up the halls and I can usually schedule to have one painter knock out multiple units in a day but even if its a one off sale, it comes across as good service for a small amount of money.In a storage area within the house or garage I will leave an unopened box of each tile, and flooring used in the house along with unopened 1 gallon buckets of the wall and semi gloss paints and one of each door hardware (kitchen and interior doorway.

Quote from @Tyler Kesling: Not to drag this thread out indefinitely but if I were to take your advice and start small, is it the dumbest thing to 1) Hire a PM on a single fourplex and 2) Do a HELOC into a DSCR?

An investor can enhance returns in the SM all kinds of ways. 

Windows would be my next check-point (less than R1) and then wall insulation: I would not be surprised if they have no insulation inside, but you can do blow-in, which only requires a small hole.A home looses heat in two ways: heat conduction (which you can slow down with insulation) and drafts, which in old houses is usually the biggest culprit.