The last time I re-seated my cabin windows was 7-10 years ago.
I thought I would be smart and used black caulk thinking it would make the windows look bigger - insert prettier here - from a distance. Given that I never see the boat from more than 20 feet away, the windows don't look any bigger.
What I did gain was a mess. The black oxidizes and the crew's feet, rain, etc, drags black markes all over the cabin sides. Of course, I was also dumb enough to use it on the inside too, ugh.
It's on my list of things to do - somewhere below installing spartite around my mast.
One additional note: I've used 3M white polishing compound followed by paste wax on the windows. They clean up real nice.