I’d find a local handyman or painter to give some second opinions. 

I am focusing more on blue collar neighborhoods.. multiple generations live in one house together, lots of painters/ carpenters etc. live in the area.

The interior was badly stained with tobacco so I paid painters to do 3 coats of interior oil-based primer and neutral gray in the other rooms.

Itemize any deduction and keep good records with pictures and written statements from the carpet cleaner and/or painters documenting the damage in case you have to defend your actions in small claims

(Low VOC Caulk only)(5) No loud music, use earpods only.(6) No personal use of toilet or sinks or tubs in unit.(7) Pour no solids or liquids down toilets, sinks or tubs.(8) Unit must be broom clean at end of job.It's possible trim and doors will last twice as long as wall paint.It's possible painters charge about the same for the trim and doors as the walls.Some painters spray, some brush some roller-- when painting tell adjoining units to close windows ahead of time to prevent dead birds, fish, other pets (or babies)--some primers (and cabinet paint) can be highly toxic and are not low VOC.Good Luck!

The painter said "Since this home has many areas of large peeling paint the surface after primer and paint will not be smoothed as before will have texture."

What may work well for your budget in Westmoreland or Washington county may not be feasible in Allegheny county.

Painters- anyone have great experiences with anyone?

They know who they like to follow painters would know good drywallers electricians know good plumbers.

I wouldn't even know how to find these folks painters flooring in Newport News, VA.