Paint the trim FIRST!
I found a great, easy tip over at Home Construction Improvement that I wish I’d seen about one week earlier: Paint the trim first. We could’ve used that advice on the Dining Room.
In the past, I’ve always painted the trim last. I think this approach is born out thinking that trim is a “finishing touch.” Everyone knows you save the finishing touches for last.
As Todd points out, painting the trim first gives you a nice paint-covered edge between the trim and the wall. And, it’s easier to avoid wall color spilling on trim than it is the other way. For the few places where you do spill onto the trim, simply wipe off the excess paint and touch up the area with the trim color.
I would add to Todd’s advice that you should first patch any gaps between the trim and the wall with a paintable elastomeric sealer. You can find that at the big box stores. Or, Amazon sells it here.
What do you think? Am I just late to the show? Is everyone else already doing this?

February 11th, 2008 at 7:32 am
Hmm… I’ve never really thought about it… makes a lot of sense!
February 11th, 2008 at 7:47 pm
Or, God forbid, don’t paint the trim at all!
But that’s a personal preference…I figure wood trim should look like wood trim. Again, that’s a personal preference that I know others do not always share… 
February 11th, 2008 at 7:52 pm
Andy - I *love* wood trim and the original wood trim look. I know that when I installed chair rail at my last house, though, the rail wasn’t real wood at all but a masonite-like material that was covered in a paintable coating.
Older homes, of course, have real wood trim — and I’m sure it’s a real pain to try to “undo” painting.
February 14th, 2008 at 4:55 pm
Alas, I, too, have painted the trim last.