I have a professional painter/ drywall repairer doing the work.

For instance, next time the painters get all the painting, flooring guy gets the flooring, etc. 

is it a single family home.. just act like it's your own.. they don't need to know what your using it for.. say it's a flip.. or your fixing up to sell..Check craigslist for painters and get references. go to a good paint supply store.. not big box, and ask who does painting they might have a good source for you. 

How many painters do you have?

Yes it can be very problematic , if you hire out lets say the drywall hanging and finishing , and they take an extra 4 days over schedule , this will push the GC"s painter out .Now that painter will have to reschedule , but they are already promised to do a 2 week job in that time frame .

Call painters, drywaller's, roofers and so on.

Can I use a painters caulking or some other type of caulking to fill these edges?

It's a very long story, but I had issues with my first contractor and painter.

Hey BP users, I'm in need of a painter and roofer.

Leave skills roles to the contractors, painter, roofers.