I spent a few minutes looking for a good caulking video and couldn't find one. Maybe there isn't one. The problem with caulking after the walls are painted is that you are going to bridge gaps between trim and walls and to do that properly, you are going to be getting some caulk on the walls so you may need to touch up. You can just leave the caulk that got onto the walls unpainted, but eventually dust will stick there and it will look bad. All caulk should be painted over. The two biggest tips I can tell you about caulking is cut the caulk tube hole very small and never finger down caulk with a dry finger. The best way is to keep a wet rag or sponge on hand so that your finger is always wet before you tool that caulk down. Also, sand all the wood that has been primed smooth before caulking and don't overwork it. Once you get the hang of it, you just lay the caulk bead on, run your finger over it once and you are done. The best caulk for trim caulking is probably DAP Dynaflex 230 or H2u which is made by OSI.

PaintGuy, I appreciate your info! Thanks,

I've been researching, too. I know now I should have caulked the trim before painting the walls, but that's okay. I've got plenty of time to touch up the green paint that gets caulk on it. I've perfected my "dry brush touch ups," too.

Live and learn.

I should now caulk the trim, paint the trim, and then touch up the green walls, correct?

Thankfully, the living room is getting all natural hickory (or maple) trim. No painting on it.

Yep, that's the correct order.

Be sure to get an elastomeric caulk that will expand and contract rather than crack. Dynaflex 230 mentioned above is one.