ughh, Id be very leery of this type of arrangement where you pay first. I don't think that is in the spirit of what the VA intends. The VA pays *the school*!
So what happens when you cut a check up front, the flight school goes belly up or runs into financial issues or whatever and they run off with your money AND subsequently, the VA money? It would not be the first time a flight school up and folds with peoples money. There is a relatively shady flight school in my area that does VA benefits this way and I thought that was an anomaly. Apparently its more common than I thought...
Some schools seem to look at dealing with VA as a burden and dont treat the students all that great as a result. No part of govt is all that fun to deal with but as far as Ive ever heard, the VA GI Bill process is relatively easy and the money always shows up about a month later. As an instructor at a competing school at the same location as a school that takes the GI Bill, Ive seen and heard of alot of students being treated poorly.
Make sure you set your expectations in advance and go in with a clear understanding of how its all gonna work. Stay on them and make sure your money is used wisely. I would stay far away of any "you may me first then the VA pays me and I reimburse you" arrangement. I'm not sure that the VA would be all that happy if they found out that is how its being done. Don't even know that it is legal for them to do. I have known some pretty solid students who tell me stories of being treated like crap while using their benefits and, at worst, some felt as though they were being milked for the VA $ while being treated like second class citizens when compared to the trust funded 16 year olds.
I'm just rambling about what I have heard, I'm not saying don't use the money, the VA is actually the easiest link to deal with in the chain.
As an alternative, I have seen people enroll in a degree program for something, whether they "need" a degree (or an additional degree) or not just to collect the BAH. You then take the BAH, which is much more per year than what they give you for flight training, and knock out whatever ratings you want part 61 and still have money left over to play around with. Of course you still have to make the time to do the coursework for whatever degree you are doing but that can be easy, depending. Just some thoughts.