How long should caulking hold up before redoing it?

If anyone is trying to remove silicone or an unknown sealant, 3M and other Mfg's make a caulk remover that works well. For removal, I typically apply the remover, cover the caulk with Saran wrap and wait overnight. In the morning, the caulk comes off in long ribbons and I use a rag with mineral spirits to remove any remaining sealant film. I had to do this to my roof as there were many different sealants applied, including roofing tar. The caulk remover worked exceptionally well.