Interesting question and a lot of good advice.
Some years ago I quit my then career because I didn't want to do the next job I was going to be promoted into. My wife and I had made a number of major decisions of what we wanted to do, and within a three year period (we thought it would take one, of course) we'd done that. These included emigrating from the UK to Australia, changes of career and all that implies. My key one was to switch to being an aviation writer (and editor) full time. Luckily Mrs JDK has held steadier jobs down meantime!
Two is good. Much more is possible than trying on your own, but as the income load shifts from one to the other, you must both e happy with the deal too. Don't take it for granted, I'd advise.
Decide on what you want - blue sky ideas, no concern of "if it's possible" - and you'll be surprised at how the cards start to fall for you. When I told my employer I quit, they gave me a generous ex-gratia payoff they didn't need to, which funded our (already planned) 3 month trip around the world. Bonuses do happen.
I'd say there's two things not outlined so far, I think important. EDowning's touched on one.
1. Do you want to earn a pile working hard for cash now, so you can play later in life, or do you want to enjoy your work and not earn as much but have longer, less expensive pleasures? Chose now, and stick to it.
2. Don't muddle careers in vintage and warbird aviation with commercial aviation. If you want one
or the other, don't see spending time in the alternate area as anything else but a stepping stone to your choice. If you enjoy both, you are in a fortunate position. There
are paying careers in vintage and warbird aviation, but few. I think we all know each other's first names...

Volunteering will network you, but an also block paying opportunities.
As a professional in an aviation career, aviation people are often surprised I'm not a pilot. From my perspective, and from what you've said, do get your licence and keep it up. It will help you talk the talk, and will open doors otherwise closed. But it's not essential, and I wouldn't go back in time to get a licence.
Network ferociously (WIX is good!) and if you want to do some DIY career path planning, the book
'What Color is your Parachute' (Richard Nelson Bolles) is highly recommended. It's got good advice about interview and remuneration negotiation technique, and also - if you do the exercises - can help a lot clarifying what you really want to do and how to get there.
HTH!