If it will be painted...I let the painter do it. If it will be stained....I let the painter do it.
I already trust my painter....do you.
That should be the question.
I always caulk my trim to the wall or ceiling if it is to be painted. It makes the job look much better when you have a wavy wall. Usually let the painter finish up after things have settled a bit.
The painter always tells me which caulk they will be using, or supplies me with it. Always check the dates on your caulk also, the big box stores have some pretty out of date stuff sometimes.
This can have a problem later with adhesion.
I am a wood worker, not a painter. I tend to let the professionals be responsible for their part of the job. I would not want to be responsible for the finish if there is a problem. I once had a guy use silicone caulk for paint-able finish..
We let him go when he searched the trailer for the board stretcher.
You know...the red one with the pulley.