And that's not even taking into account the regular tenant BS.

If you do not regularly file for evictions, you'd best retain an attorney. 

If it's beyond the regular duties, then yeah, a fee for his time is valid.

I have always imagined getting to the point where I could hold/ run a small community of mountain cabin rentals or a guest house, something along those lines.Thanks,Chad  Yes I meant AirBnb and Mid-term rentals, rent by the room, glamping (although I probably wouldn't go that route), buying commercial RE and running a business (for me that would be a lot of work with a W2 job and buying property locally or leasing out a space is expensive here). 

I then found 3 properties from wholesalers in areas that I invest in regularly and purchased the properties with a hard money loan.

I just want to hear from regular investors about their experience.   

This forum is super helpful too so I try to regularly review what’s going on and be as helpful as possible. 

I would shoot him regular updates to keep him in the loop.

There's actually some deeper nuance here than just the holding period. 

Quote from @Stepan Hedz: Selling fees (estimate), $30,000, and holding costs?