When it's impossible to hammer the fascia board back and you're left with a gap between the bottom board and the fascia board... Is it worth caulking then? I find all caulk tends to crack over time.
I have a few boards that are starting to become bow-shaped and can't be forced back against the bottom boards, but I think it's probably better to replace them completely than to caulk.
- But maybe I used the wrong caulk, or not enough caulk, when I've experienced it cracking and leaving a gap again.