I don't usually post in this section, ever, but I saw your post and wanted to pass along some info. that might clear up a few things.
It's good that you have a long-term plan, but if you are going into the military don't discount boot camp, people still
die in basic training.
If you are serious about going into the military then you need to read a copy of the
Ultimate Basic Training Guidebook
Sgt. Volkin answers common questions and informs new recruits of what will be expected of them.
Here is another page to read, pay close attention to number 1.
The Top Ten Things to Expect When Preparing for Boot Camp
Also, a good friend of mine has been in the exact same predicament that you are in, with a difference of some parameters and he said that the only way he would go into the Navy was if he was a
J.A.G. - Judge Advocate General, or a Naval Officer-Attorney. Have you considered tying that in to your plans?
Best of luck.