How long should caulking hold up before redoing it?

I use Lexel on everything but the roof. I do the best I can to remove every bit of the old silicone before recaulking. If the new caulk is pulling away, that is probably due to a film of silicone that has remained. It’s pretty easy to remove the silicone bead, but that film isn’t.
I’ve used a combo of GooGone caulk remover and a razor blade to remove the film. Still a PITA, but much of nothing will stick to that film.