I’d be very hesitant to put clips on a horse that has pulled shoes this often. You’re more likely to have a lot of the hoof wall come off with the shoes, particularly if the wall is already somewhat weakened because of multiple nail holes.
As others have suggested, pulling shoes this frequently is often a function of a bad trim and or bad shoe placement on the hooves or both. Posting pictures would help inform some of the opinions you’re getting.
Having the horse go barefoot would certainly fix the problem of the horse pulling his shoes off. But it wouldn’t fix a bad trim or bad hoof balance if that’s the underlying issue.