I finished my tour of the big-three paint companies and each offered helpful information. I spoke with the contractor and his crew can do the carpentry jobs before painting. As for paint he has one of the companies he prefers, but I can look at the color chips from all of them. It makes sense to go with a company where he gets a contractor discount, so we'll see what is available when we have more time to talk.
The contractor works mostly in a historic part of town six miles north of me but his painter lives in my village so this job would be convenient. I'll give myself the weekend to tidy around the yard, mow, get some of the garden beds into shape, and have access to all of the spots I need painted, though it won't start for a while yet. Ducks to line up: I need to consider the rickety patio cover in the back that will be in the way of painting so should come down now. Replacing it later with a kit will probably be done by my handyman friend - we've had numerous conversations about when but it looks like "soon" is when that will happen. Bonus question - if they can replace the sliding glass door on the back I'll kick in extra cash for that.