If it's meant to be it will be. Initial Officer taining is quite strenuous, and they aren't allowed home for the first 4 weekends. And they sometimes get weekend restrictions, where they have to stay in due to doing something wrong, or someone else doing something wrong.
However, once they get through basic training and move into the College Hall Officers Mess, it becomes slightly more relaxed and you can go and stay, bearing in mind they have very busy weeks! They have functions which you can go to - Mid Course function (cocktail dress do, informal) halfway through the course, and the Graduation Parade - watch him parade, and then lunch with them and a massive party in the evening. This is only for around 8 months.
After that, he could get posted anywhere in the country before starting flying training at one of three places (in the midlands area) which will be for a few months. Once he is in a mess having graduated, you can go and stay whenever. The bar is cheap! And there are many mess functions during the year which are brilliant fun (and cheap) - Summer Ball, Christmas Draw are the main two, but they may celebrate things like Valentines day, oktoberfest, halloween etc.
Just remember, the first few years are likely to be stressful - flying training is just that!!
Things happen for a reason and if it's meant to work...it will.
Suggest you post in armed forces - there are a few people seeing military personnel, and some current mil people as well.