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Thumb Sucking

My son is 5(turned 5 in August) and sucks his thumb, he started at about 8 months old. I am not sure what to do or if I should do anything at this point. I have tried incentives, with charts and prizes and praise and talk of being a big boy. This works about 90% of the time during the day, he needs reminders and usually when I do remind him he says "Oops! I'm never going to suck my thumb again!" But seems to forget an hour or two later. At night his thumb is frequently in his mouth(not really sucking just there) I have tried band aids, funny tasting stuff, gloves... etc and he just takes it off . He does do it at school and his teacher is okay with it and agreed to help curb the habit when we let her know we're all ready. Also he does not get made fun of at school for it, so that is not an issue.
He was born with a large overbite(from me, my mom, my brother etc we all have a recessed lower jaw) and I know the thumb sucking isn't the cause of the overbite(although the dentist thinks so) but it's certainly not going to make it better. Whether or not he sucked his thumb he would "need" dental work when he's older so that isn't a huge motivator either. His dentist wants to put in a fixed palatal crib and I'm not sure how I feel about it. I know he does it for comfort and because he's insecure. Our lives aren't very stable right now and I feel it would be mean to take away his comfort at a time like this. I know how it feels too because I sucked my thumb as a kid and when my mom tried to get me to stop I got all butthurt because I felt I needed it.
Also he has two adult teeth that are crooked and pushed back from where he sucks his thumb. I worry about his adult teeth being messed up.
Before anyone says "No one goes to college sucking their thumb" yes, they do. I know many teens and adults who still suck their thumb. A lot of them tell me wish they had more help stopping as young children.

Any advice? Has anyone had an oral appliance used on their child that worked? Didn't work?

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