Caulk is Pulling Paint from Wall
I noticed the other day that the caulk has pulled away from some baseboard. This area was caulked by a carpenter. But instead of just cracking, it's pulled the paint from the wall instead. (All the way to the old paint and bare drywall beneath. There are some problems with the original 40 year old builders paint flaking off to bare drywall. All walls were Gardz'd and as far as I know, this one was.)
This was caulked maybe 5 months ago, long after any painting. I'm not sure when it pulled away but haven't noticed it until recently. I think I would have noticed this if it had happened shortly after installed.
How would you fix this and what to do with all the rest of the caulking that needs to be done so it doesn't happen all over.
Not the best picture.