Money, variety of interests, & season length are issues for me.
I'm a college student, though I tend to hold down well-paying jobs (even if only for summers) so my budget is OK but not big by any stretch.
I'm currently on a rather old axis 172, and shopping for something similar-ish in metal, yet affordable. Ive talked with one person, and their offer seems intriguing. Grabbed my 325T boots used but in quite good shape, ditto for the snowpro race bindings.
As far as other interests,
I spent a bit on photo supplies this semester- mostly paper, some film, an incident light meter. Had the camera/lens already. Bought the film body, digital body, and 2 lenses used over the last few years.
I also sail, windsurf, and surf. No major purchases here lately. Family has a racing sunfish, I'm pretty content with my current board, sails, masts, booms, etc. I think windsurfing matches the excitement of carving. Surfing is cheap too, once you've bought a few boards.
Biking, spent a bit here in the last few years. Most of the gear used, or discounted, though. C'dale capo frame with top end crank/BB, some pretty good wheels & other components. Amazing how much weight you can save when you ditch the shifters & cassette
Relatively content with my (bought new) specialized mtb from 2000.
May be selling my geared road bike, spare track frame, and building up a geared TT/Tri bike. That & the capo would fit my needs.
Longboard skateboards aren't too expensive when you build your own decks, and selling a few covers the expense nicely.
I've ranted enough. Point being, there's too much money to be saved by grabbing used gear for me to go for the brand-new stuff right now. When I'm making a bit more (if I still have time for many days on the mountain) I'll look into a custom board. This is the one that seems especially worth buying new. Not a lot of benefit to brand-new bindings or boots, so long as they're the same as you would have purchased otherwise.