Ahhhh, the Eagle! One of my favorites.
Welcome to the forums! We're also AD USCG and are stationed down in Cape May, NJ at the TRACEN. Hubby is 19 years in and looking at another 11 until he retires fully. We have the liveaboard/circumnavigate/cruiser dream on a 41' but until we get the necessary funds saved up, we're starting off smaller with a 22' to learn on. Much like you, a whole career afloat, but none on anything w/ masts and riggings, so we're definite beginners.
There's a lot of hugely helpful info here about monos vs. multis, cruising on budgets, cruising on military pensions, best drinks and music
for cruising (two of my favorites!) and a wealth of engineering, manufacturer, liveaboard
info and a bizillion other threads more. If you can't find it here, I'm sure it hasn't been thought of yet.
The general attitude is whatever gets you off dry land, go do it! Chase the dream, live the life however you can and create your own opportunity. Life is precious and much shorter than we all like to believe...
Fair winds and following seas, my fellow Coastie!