How do you know when to stop saving?
First, congratulations on your retirement-- whenever it may happen! Don't wait on the Air Force to make up their mind-- get yourself to the retirement class now so that you can start your own preps. You might want to check your base library or public library for a copy of the book, or read the first six months of posts on the blog:
http://the-military-guide.com/post-titles-by-month/Second, if you're not already doing so, make yourself a spending plan instead of a savings plan. Give yourself 10%-20% of your income to spend on anything you want. Put it into a separate savings account if you have to, but start tracking how much you have in your "entertainment savings" account and keep trying to either spend it on a goal or just spend it down to zero.
Third, again if you're not already doing so, check your budget and make sure that you're tracking everything. You'll feel much more secure knowing what you're planning to spend that month and how much more you have left over for surprises or emergencies.
Finally, consider throttling down your savings rate to as low an amount as you feel comfortable with-- at a minimum, try to save no more each month than you're trying to spend on entertainment each month. That way you have the comfort (savings) as well as the flexibility (entertainment). You can say to yourself "I'm already saving that amount this month anyway, so I can afford to spend at least that much."
Otherwise, you're right about your feelings. You can keep tweaking your budget until you figure out what type of spending brings you value. Until you get comfortable with your retirement spending, you could try a number of different activities to decide what's the right ratio of pleasure::expenses. You seem to have plenty of room in the budget to explore your interests.
My spouse and I have been retired for nearly 12 years, and the balance in our checking account still rises almost every month. However we're happy with our spending, we enjoy the activities that we're spending on, and we don't feel as if we're depriving ourselves of anything. We may occasionally feel that we need to "earn" it, but we don't deprive ourselves.
You should go see a Buffett concert. He's not going to be performing forever, and you'll kick yourself if you miss the chance. Buy a DVD or stream a show and see what you could be doing in person.