Question about painting trim before or after installation

I got into a BIG argument with my neighbor Dave last Saturday while we were both working on our houses. He swears you should paint ALL your trim before you install it, then just do touch ups later. I've always installed my baseboards and crown molding first, then caulked the gaps, and painted everything after. He said I'm creating more work for myself and the lines will never be as clean. But I feel like you get a better seal between the wall and the trim if you paint it all together. Has anyone here actually tested this both ways and seen a clear difference in the final result?

2 comments

2 Comments

anderson.jason4d ago

Heard my buddy Mark say the same thing Dave did and now his caulk cracks every winter.

wesley_fox924d ago

Wait do you mean like actual caulk for windows and stuff? My buddy Steve used whatever was on sale at the hardware store one time and the whole trim job peeled off by February lol. He tried to fix it with some cheap silicone from the dollar store and it looked like a disaster zone. Now he just uses the same brand his dad used for like 30 years and hasn't had a problem since. I guess sometimes there's a reason people stick with what they know even if it costs a few bucks more. But man, seeing that caulk split every winter would drive me nuts.