We originally got it for fear of the heat pump going bad, but it has paid off for a new washing machine and refrigerator, as well as repairs for the hwh and central air.

Then, turn on every faucet, shower, and washing machine in your house.

In Portland there was a huge deal with a painter that pressured washed and scraped an old house.

For rental properties I know you can depreciate things like a new roof, new washing machines etc...although different things have different schedules of depreciation.

Vinyl siding should last almost indefinitely requiring little than cleaning.I would power wash it every 10 years or so.

Or would this end up just being a wash against our primary residence?

You're not doing yourself any favors having that stained carpet in the house, I'm surprised your realtor didn't recommend replacing it off the bat.If that fence wasn't painted, you can have it pressure washed. 

Might as well put in the document that the squatter must mow the grass and wash your car every week too.

Not only is the house constantly filthy, the trash builds up and rarely is the house ever given a good cleaning besides dishes being washed, we aren’t treated with respect.

Set up has 1 detached unit with its own water heater, and 2 attached units with two water heaters, one of which supplies water for both attached unit washing machines.