Well, I can answer your question pretty easily. In the order you have, it's not going to happen. Been trying to get them to do it for 6 months. You basically have three choices. 1. pay for school using loans, join the Army, and get loan repayment. 2. pay for the first year of school in loans, apply for HPSP, and hope you get the next 3 years paid for, become a vet on AD when you graduate (they also have 2 and 1 year scholarships). 3. pay for vet school with loans (see a trend?), join the reserves and receive a $75K sign on bonus and get $250K in loan repayment.
I suppose I technically have gone in the order you have above - I joined the Army, did some time, and am going to pay for a lot of it with Post 9-11 GI Bill, yes, that does work too. I don't recommend it unless you are really patient.