I think looking back at older work and cringing is good and healthy, it's a way to know that you're improving. I'd be more concerned if I looked at old drawings I made and DIDN'T cringe, because it means I stagnated.
Definitely. There's a lot of photography I have online that's fucking embarrassing and makes me laugh, but I wouldn't ever get rid of it because of where I got from that point. It also helps if you're in a rut to remind yourself of how different things are now. It's just part of the creative process. Always another cocoon to break out of.