Paint I am not worried about, maybe at the end some touch up. 

So, you are filling holes and dings and touching up paint anyways.

If you actually have to work one on one with people and dig deep into their situations, touching millions is not feasible nor is it some personal goal of mine.  

I wound't touch a house on the beach/ocean. 

and of course let's keep in touch, now we are connected

This fee helps cover cleaning and paint touch-up costs after tenants move out.

I am in the process of putting final touches on Irrevocable Trust and Delaware Holding LLC with my attorney. 

I've been using it for a while now and it has so many great features, many of which you are touching on with your questions. 

If you are getting a long term rental, you may have some upfront work, and then whenever a tenant move in / out have some work, but typically for long term rentals you aren't touching / doing things to it every day. 

For your major capex expenses, I assume AC, WH, roof, you would need to get in touch with a local contractor (or two).