Well, that was a long read. As an Active Duty USN enlistee going on 12 years and being that I just got off a mid-watch - You're about to be an Officer and you said YOLO?
Allow me a minute to gather that.
Ok, now that that's done, if you have over $32K of "capable personal financial pool to tap" and your parents have 3/4 of a MILLION in the bank (which is a mistake if they're leaving it in the bank, trust me) -- why in the HELL are you coming on here and asking us what you should do?
However humble that is, this is what I come to as a conclusion:
They're meeting you $1:$1. A new fully loaded Raptor tops out around $57,000. You have a tangible $32K. Combined, that's $64K. You're $5K over. My own recommendation would be to take $16K of yours, $16K of theirs and drop over half down on a new Raptor and then finance the rest and set up some auto payments through USAA and get that credit going.
But, assuming you have incredible credit coming from a wealthy family, do what you want. Aside, YOLO!
Do you want the damn truck? Get it. Are you unsure? Don't get it. What's the maintenance costs? Normal. Does it break more/less than a "normal" vehicle? It's guts are nothing but an F150 and they're the best trucks on the road.
Your questions are a bit outlandish, but we're all biased here.
As I said, I'm AD USN E6/CTN1, been in for 11 years, up for Chief and dropped $17K on my third Raptor. I think that you can make a great decision based on what you wrote above yourself; that's my vote.
\\EDIT\\ You have no intentions of getting married in the next ten years? I don't know man, sometimes them women come outta nowhere and slap you in the face with your own right hand and it just happens. Hell, you might even meet one that has her own Raptor and Dyson vacuum cleaner! It could be the most incredible thing and I don't think that you should even consider a truck making a difference in that.
Thinking about this more, I absolutely applaud you on thinking out this purchase so intricately, something many people (Military or not) do not to when it comes to making decisions. But I don't think that it's THIS big of a decision. That's me. I've made the decision three times already and loved every one of them. But I bought a house when I was just over 28, too...so what do I know? I've been better off than I am now, but I've been worse off too, so I could be talking out my ass, too.