He can't wait until June to decide and then leave in July. The process to leave takes 3-9 months, depending on a lot of factors. He has to decide NOW if he wants to leave in July. The Air Force is already slotting people for July, and we're about to start on August slots.
For the Air Force, he can get in with those charges if the fines were under $300. If the fines were over $300 he needs a waiver, and that adds even MORE TIME to the process.
He will live in DORM rooms on base, and she can not live with him if they are still girlfriend and boyfriend. If they are married, he'll get a house and they can live together. But, this will be unlikely to happen by November. He has to get in (already looking at July/August if he signed papers today), then get through boot camp, and THEN get all the way through technical/job training. Job training can be a few weeks to a year. If it's longer than 6 months she can move with him (if married), but if it's 5 months and 29 days, she can not. So, November... highly unlikely.