The portion you rent out can be exchanged pretty safely once it’s on 2 tax returns or 2 years, and occasionally faster depending on “intent”.

You can look  into executive rentals which normally require fully furnished and stocked ( dishes,towels and bedding ) but you can get a lot more rent and normally get a lot better quality renter, some downfalls though is it is normally short term but sometimes you can get lucky and cooperation's will lease it for the year and send differant people there periodically.

So you do end up "paying" for maintenance.And please don't throw out the canard of the "problem-free" month where the PM does little work, you have to look at it through the cycle, all the hours spent on finding/placing tenants every year or two, serving 3-day notices, occasional eviction/setout, dealing with problems that crop up, arranging for repairs (God forbid getting multiple bids!!)

My issue is that my official roommate A occasionally threatens to lock B out of the house.

Patch once in a long while, seal about the same, sweep occasionally maybe every six or twelve months, paint stripes once every few years maybe five or ten, replace an occasional concrete stop bumper or sign, paint the light pole once every ten years or so. 

I have sometimes had move-ins on the same day as a move-out, although it can occasionally take a week or two to secure a new tenant.

Easily over 10mil with an occasional deal and I certainly didn't start with anywhere near $772k. 

We do occasionally have a train that comes by the cabin, It has a schedule and fun to watch go by if you are happen to be there...bla bla bla."

Really, as other have said the key is to get the unit clean with no open food containers, no dirty dishes, and especially no water.

Before bed, the dishes should be washed, stored and the counters wiped dry, close off the drain with the stopper and spray entry points with smelly disinfectant (roaches hate this).