There is some minimum that seems to work well enough in a lot of hobbies. Can't always go for the cheapest, but you may not have to go that high, either.

Amateur astronomers tend to hate on Walmart telescopes, and there are reasons for that. Still, the optics in any of them are better than Galileo had, and he saw a lot (admittedly, he also didn't have a hopelessly light polluted sky). It's a matter of setting expectations.

A $25 Baofang can get you into amateur radio after getting your technician license. There's even a version now that doesn't spew spurious emissions on harmonic frequencies and fuck things up for everyone else.

I once traded a somewhat older GPU for a fretless bass, amp, and effect pedal. The guy had just moved, his GPU died, and seemed like he wanted to get rid of some of his stash. While that was an exception, there's probably some guitar guy in your city that wants to clear some stuff out and is willing to make a deal.

I started off with a Canon Digital Ixus as the first ‘real’ camera that I bought. Absolutely adored it. A full metal build and about the size of a cigarette packet. I took it everywhere and shot a few vacations on it.

But it honestly wasn’t until I got my Canon EOS 350D that I could actually attempt to really learn photography. Because now I could use manual settings, learn how to use them, use filters, try new techniques, get more creative, etc.

When I needed to invest in something like a flash, tripod or lens I always applied the same thinking: buy it so it can grow with you. Of course, eventually we got full circle and I ended up back at analog photography developing B&W Minox film in my kitchen :D

Anyways, I’ve never regretted buying better, but I’ve definitely regretted cheaping out. So I don’t if I can avoid it.