@Rainmaker1973 1) Why would you lean a ladder against a gutter? A lot of them are are flimsy and would crush. 2) Why would you attach your ladder to a flimsy gutter that could rip off at any time. This tool may work with something else. But I wouldn't trust it on gutters.
@interesting_aIl Why caulk there at all? Leave it as is. All caulking does around baseboards and cabinet bottoms is collect dirt. It also stains and makes it harder to wash the floors.