I would stay away from silicone as it is not paintable and I
have had serious problems with its adhesive qualities on wood
and masonry.

I agree wholeheartedly. I'm sure there's a "paintable" silicone
available, but my experience with silicone adhering to wood and masonry
is that it doesn't. I hate to see it on a house, but if it needs to be
ripped out it's great. It comes out out in nice long strings.