So we recently had a sewer backup in our basement when our initial basement finish was 99% complete. This has been one of the worst experiences of my life :-(. Anyway, being we have had no success in getting the city to pay for any of it, (it was their fault) I'm trying to save us money where I can. So to save us money I'm doing all the painting. Every thing has gone fine until my contractor went to install our doors. When he went to install the recessed pull on the barn door and cut out the hole for the pocket door. On the pocket door he said the paint just started peeling off and he even put tape on before cutting. On the barn door he didn't do a great job chiseling out the recessed handle.

So my questions are 1) why do we think the paint peeled? It was preprimed and I used Sherwin Williams Emerald paint. I sanded out the edge of the peeled paint, is that good enough before painting again or is there still going to be a visible edge of where the paint peeled off? Should I prime the already primed area where the peeling occured?

2. On the recessed handle he filled the gaps around the handle where he chiseled out too much with caulk and it looks bad in my opinion and you can say I'm being picky but I am picky :) So question is what can I fill this gap with instead of caulk so I can sand it smooth and it looks more natural? Can I add wood filler over the top of the caulk or do I need to cut the caulk out or would you recommend something else?

Here are some pics, hopefully that help show what I'm talking about.