If I may offer a completely different perspective. Friend, you haven't lost your drive, your desire, your motivation. You've lost your heart. If you think that you'll be able to jump to the Navy, Marines, Air Force, Coast Guard, Homeland Security (all of which have flying) and that said flying job will stir you back to who you want to be by scratching that itch, you're wrong.
Oh, don't hear me wrong. The itch is real and so is your disgust with your current situation. Very real, very valid, very potent, and very very treacherous. From what I can hear, the solution you are seeking isn't the real antidote...it's a band-aid...granted, it's a very comforting one, but a short term solution none-the-less. Unless you get your heart back, you will get bled dry by a thousand other tiny cuts that any other institution WILL inflict. The USAF did it to me when I was about 27, and many other's on this board will attest to the same. You need to get your heart back so you can endure that course.
My recommendation is to definitely go snowboarding. Take some time to clear the perspective...preferably without a smart phone. Decide about quitting your job afterwards. Take a book with you too: "Becoming a King" by Morgan Snyder. Only 200 pages. It might help you re-discover the real fire and where your heart went. Without your heart, nothing you try will succeed. Rediscover it though, and you're in a whole new ball-game.
What I hear about your work situation could benefit, in the short term, from an adjustment of perspective...the cubicle is not the prison, it's the enabling water-fountain and or spring-board to finance your real career/adventure/commissioning. Endure only as much as you have to. Don't jump early, but definitely don't jump late. Leverage it until you don't need it anymore...and it sounds like you still might need it...but I'm just guessing on that last part.
Afraid of money mistakes you've made? Ok, don't make those mistakes again. It don't mean you're dumb, it means you've had an experience and learned from it. What you've done DOES NOT define who you are nor what you will do in the future, unless you let it.
Go get your heart back. You want a change of career into flying and you won't take no for an answer? Ok. Blitz through your instrument and commercial ratings like you mean it, and start flying night cargo. I'm being completely serious here. Do it. Quit your job and hang it out there. Do it, live in squalor for season, make some mistakes, learn from them, and move on. If that's what it takes to get your heart back, it's FAR better than moving from bad situation to bad solution. That road...the one where you fix today by jumping to what looks like greener pastures in the military...(as several here have alluded to) will only lead you right back to the discontent you feel right now, only it will be worse, because then you'll be saddled with a 8-10 year commitment to the military that you have no choice about.
Go get your heart back (pro-tip, let your wife know what's going on, but do not look to her for the answer of finding your heart), then go get your flying career. If those goals coincide, all-the-better, but measure the cost first. You may decide to wait, but don't stand still. Standing still is indecision. Waiting has purpose, meaning, and a trigger to end it. Whatever you do: Don't stand still.
FF