Caulking the outside

Removing all the old caulk first and using masking tape on the outside of the bead of caulk will assure you of a nice looking job

Geocell Proflex for everything but the roof. You got to remove old silicone 1st

If you're going to be on your roof, it will be a good time to apply Eternabond to the seams and edges.
Just a thought.

Dicor has two formulas. One for roofs and another for vertical surfaces. Others like Proflex. I was never able to get it to stick.

On the siding for windows, corner moldings, I use Proflex