If you painted it in 2013 with a decent quality paint you probably don't NEED  to paint again now it might spruce the place up a bit if you do but the paint should not be failing. 2) So your cost for this paint job is $1600 in lost rent plus the $1092 mortgage that you will have to cover out of pocket, if you take that $2692 would it cover a professional painter? 

The tenant has to move out by noon on the last day of the month and they just leave the keys in the lockbox, the cleaning company comes at noon and uses those keys, the painter comes at 3 pm and uses the same keys, if there was damage I noted in the pre-move out inspection I leave the supplies in a common area and have the handyman over in the afternoon.  

The painter, turned out to be terrible in what he had done so I had to do it myself.

Call 10-20 roofers and get roof estimates, call 10-20 tile guys and get price/square foot estimates for floor tile and shower tile, call 10-20 HVAC guys and get estimates on a 3, 4 and 5 ton unit, call 10-20 painters and get a price/square foot estimate for interior and exterior painting, etcYou could also call GCs and get them to a property to bid it out but just know that, especially in this market, a GC is going to charge a lot and that will sap a lot of your profit vice managing subs yourself.

I had painters and new carpet coming those first 2 weeks of January and the house needed to be empty. 

Is this something where you need a general or can you use some high quality subs like painters, flooring guys, etc? 

But I have a painter, cleaner and landscape guy on my team.

Contractors / flippers might need part time painters, or trash out guys...then there is mortgage field inspectors, which can be a gig of its own.  

I recommend The Encyclopedia of Commercial Real Estate Advice by Terry Painter.

We are residential and commercial general contractor and developer and we are looking for professional painters and floaters for our residential developments.