I've had a lot of experience transforming wood stained moldings in the past year. I paint the trim first and then cut in wall paint. I would start with an oil based primer and then two coats of semi-gloss. I've had good luck with SW products but I also see BM is very popular on this forum. You can search my user name and there should be a couple threads of my den area that was recently transformed.

Good luck!!!

Thanks waltbsc, I will check you out lol ;)

Choose the wall color first.

Thanks htnspz.

waltbsc, wow! Your room looks really great. I am really inspired and motivated to paint the trim now. Thanks so much.

I pick all my paint colors at one time. Ceiling, wall and trim. I make sure I look at the paint chips in the room I'm going to use them in in a variety of light. Both natural and man made.
I always start by painting the ceiling and then the walls and then the trim. When you use a roller or even a paint brush you learn pretty fast about drips and splatter.
It's alot like when you clean . You start at the top and work your way down so any dust or dirt doesn't ruin the work you've already done. Same with painting. Start at the top and work your way down.

Definitely paint the trim first. Then the ceiling and then the walls.

Or ceiling, then trim, then walls. It's easier to paint the trim and then the walls.

Thanks everyone!