Ike,
Welcome to the forums and thanks for your service to our country!
The Ultra's an excellent bike, my bro-in-law has an '09 and he loves it...there are a lot of complaints about heat from the engine on HD's but even here in FL I find it tolerable on my Street Glide. I've read some things that once you get your air intake, exhaust and ECM updated to run richer rather than lean, it helps some with the heat.
The synthetic oil thing(?)..not sure what your concern there is but HD makes full syns for all it's fluids that need to be changed. Also, a good many riders have found some others that they like from a personal preference stand-point.
Dealership's working with you on MSRP? That's gonna be a tough one unless someone here knows something about the dealers local to you...it's all up to them. Here in FL there are some that will and some that won't...
Again welcome!