Some time ago, I got a hold of a 1966 body in really rough shape. Mostly nicks and scratches and a weird brown paint in the pickup cavities, but hey, I got it for really cheap. Anyway I installed the neck, i have both a gotoh and a reissue standing by for installation once i get the pick-guard and electronics sorted out.
Anyway, I knew the strap button over the neck was damaged (like the button was ripped out completely), but what I was wondering if i refilled the original hole and put the button where it originally was would it hold? Here are two pictures of it for reference


The button on the bottom of the guitar was also damaged. It looked like some one either tried routing it out by about a quarter of an inch and at a slight angle backwards or dropped it right on the button. The original screw still fits, albeit very awkwardly.


Any recommendations and advice is welcome!
I have considered re-drilling new button locations, it would end up being the most painless solution, but I want to see what options I have.
Thanks guys!