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I think we need a price point per period time you're willing to spend to make your life interesting. I know that sounds seriously ridiculous, as there are plenty of exciting things to do that cost nothing... but those aren't nearly as cool to plan out!
My thing, back when I had lots of time to do whatever, was to pick one thing that I thought was interesting and become as good as I possibly could at doing that thing.
For a while, it was kart racing. Then rock climbing. Then freshwater free diving. Then honed skills as a machinist. Then TIG welding. etc etc.
This is one example: Buy an old 911 and turn it into a track car. Sure, you'll spend $35K. But if you do every bit yourself instead of farming it out to a shop- that $35K becomes more like $25K and by them end you'll know a hell of a lot about welding, wrenching, paint, fabrication, and electrics.
Just one example. The same process can be applied to fixing up a boat, or rock climbing (slings, quickdraws, shoes, harnesses, carabiners, cammers, rope, etc), etc.
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