I know I cannot use "my own labor" costs if I do work on my own rather than hire a painter, but can I somehow use my time lost at work/vacation time used for appointments related to selling/repairing, etc.?  

My painters haven't done it before and I want to know how easy or difficult it is.

Depending on the type of "group home" (drug/alcohol rehab, handicapped, mental illness, elderly, etc.) you have other laws to make sure you comply with, and great point by David D Painter re insurance.

I've used different pest control companies, handymen, flooring guys, painters, electricians, etc., just on these 2 properties and feel like I have a solid grasp of what to recommend. 

We were a very cool space and had everything in terms of tenants from painters, photographers, cleaning service, community groups, etc.

Denver street / grafitti / mural artist or community group to paint the side of my building (great exposure for their work, 50,000 cars/day)2. electrostatic painter or auto body worker who wants to moonlight and restore my metal cabinets lowrider style (think glossy turquoise or black with pin strips)

As Micki M. said, walking through with your project manager is a good idea, but definitely start trying to form relationships with painters, roofers, flooring installers, etc ASAP!  

Pool has been resurfaced.Sod: $1,550Paint: $4,400Tile: $4,700Pool Resurfacing: $2,000Next on the agenda is replacing interior doors and baseboard, installing cabinets and countertops, and getting the painter back to finish the trim, doors, pool deck, and garage floor.

You need a Demo guy or handyman Plumber Painter/drywall guy HandymanShop around and price the material yourself to get an idea of the material costs.

I have joined the REIA in Owings Mills on Painters Mill Rd. but I have also started my own REIA BP meetup group here in Bowie.