I've tried asking if any maintenance was needed in various ways and never got a "Yes" in any form, even when there were obvious problems, such as paint peeling off the ceiling and a wired smoke detector hanging from the ceiling by the wire.

My SFR is well maintained with all walls intact, newly painted and orange peel textured.

JDI don't know if I would paint POH residents with such a broad brush. 

Full kitchen and bathroom remodel, new floors, drywall, interior and exterior paint, landscaping, and misc.

Peeling paint was always difficult.

I believe that will be a paint point for you and may be better to simply buy a recently constructed building where there's less risk and far less time involved.

TLDR, it's like a 5 gallon paint bucket filled with money.

Your situation sounds like a classic investor's dilemma, and it's great that you're considering all angles before making a move.First off, it's worth considering what the "rip cord" would be for your investment—essentially, what's your financial breaking point where you need to make a decisive move to avoid further losses?

We are looking for people to paint homes/kitchen cabinets, countertop companies and lay tile in the Tampa area.

Go into Home Depot and see what a gallon of paint sells for.