I do inspections without the contractor present and mark punch list items with painters tape. 

My painter was there at the time and he's a young, full of energy type so I let him do most of the work (with a bonus of course).

We had an amazing 12 member maintenance crew, and a painter who refused to give his age so he didn't have to retire. 

Any recommendations for painters to use to repaint after a tenant moves out?

We have a PM, but I also have built relationships with other professionals (landscaper, flooring guy, HVAC guy, painter, handman, etc.) in the area because I'm more comfortable with the vendors and contractors that I have had complete work on the house before.If doing everything yourself, I'd imagine that "how far is too far" is really only a function of your own tolerances. 

Such as Inspector, Painters, Contractor, HVAC team etc.

Out of 100 painters 2-3 of them will be able to deliver a truly professional HVLP paint job.

I also have a local, retired painter that loves to do local projects.

She did a phenomenal job, almost as good as my professional painter would have done, with no spills, runs, etc.

@Jon Franke I have a great painter that may be a good fit.