It took me about six months before my picks felt comfortable but now I don’t even think about it. However, I play reissue National NP2s which I find more comfortable than common Dunlops.
Probably a lot more expensive than your idea are Shelor picks. They are really painless but for some reason, at least for now, I like the Nationals more (maybe I’m just more used to them).
But I think once you spend enough time with them, you get used to picks.