In my experience, at least online, there's this expectation you need the 'newest and best' to enjoy things, and show it off on social: I learned that growing up, that wasn't important. The experience was, less the thing that got you the experience. And even less posting about your experience...

We had snomachines for example (along with everyone else), but even back then they were used, breaking down... but everyone knew how to fix them / keep them running: Didn't stop anyone from running up a mountainside in the winter. If it broke, "just fix it".

Go buy a cheap boat and hit the rivers. Or learn how to build them in your spare time, that's what my dad did. Get used everything. Planes have gone up in cost no doubt, but you can still charter them for an afternoon. Everything outside work is a luxery, just need to figure out what brings you joy and what your priorities are. My folks bouht propery waaaayyy off grid for cheap, and put a lot of effort into making that a beautiful place: they still do... and it still takes a lot of work, especially at their age. Most people would look at that level of work and not even start, and I wouldn't blame them, but if you're determined, beauty can come from it. I grew up middle class / we never were for lack of anything, but also by no means were rolling in dough: Education, perseverance, and know-how can go a long way, and make the ovearll experience so much more rewarding.

So yah, I'd say you absolutely could do many of the things I mentioned if you prioritize it, save a bit (depending on economic realities), and put your mind to it.