Lol, I understand! How old is he? I put a collar on Jackson during the first week of having him home. I definitely would try to get little Toby used to the collar now rather than later if you're going to have him wear one.
He may try to bite at it or be annoyed at first but he will get used to it.
I sometimes take the collar off of Jackson at nighttime just for comfort purposes. He doesn't go in the crate anymore so I don't worry about that but I would definitely take it off while he goes in there like you said, so it doesn't get stuck while you're not home. Also, make sure it's not too lose (or too tight).