This is how we're doing our December trip. We have two members with military i.d.'s in our party. Mine is a spouse i.d. from my pending divorce (we're in separation at the current time) that's still valid. The other is my boyfriend whom has an i.d. also.
Tickets: 4 day park hopper promotional tickets, 2 tickets per person (thus getting the maximum allowed per i.d. = 6 (3 people) and then the other person buys 2 on his i.d.
6 day tickets:
Tickets with Military promo = $1,104 (NO TAX!, if bought at ITT or SoG)
Stars and Stripes tickets = $1,396 (but includes water park fun and more tickets)
Regular WDW tickets at Rack rate = $1,256 (park hopper only)
We chose the promo tickets because it was easier to buy two sets and use them back to back instead of buying one set and then a two day ticket.
This is our final option that we decided to go with in December.
Two value rooms at All Star Sports (includes KTTW card, free parking, EMH, and all WDW perks. Military discount for Value resorts = 30% possibly 35% (that's what we got).
Total for room = 922.00 (with tax) 66.50 for weeknights, 73.50 for weekends.
Try to go during the week, weekend rates are higher!!!
The two rooms was a better deal because of the type of party we have, it's four adults and we like our space. Versus one room at SoG for 105 a night, or two rooms at SoG for 210. PLUS the parking.
and purchase tickets at SoG upon arrival. If you choose to purchase the military promo tickets at the gate you will pay tax on them. If you purchase at ITT or SoG you will not pay tax.
Also, if you're going to fly. Delta and Southwest have military discounts. (I would talk to your ITT about that though)
Military discounts for Resorts go like this = 30-35% Values, 35% Moderate, 40% Deluxe. You don't get much difference in space except a few more sqft going up in classes. Mostly just about location. Also, book ahead in time, resorts have a limited number of military discounts they can give out.
Not sure about
DDP, never used it. We like paying OOP for meals.
Hope this helps.