For tools, I buy the cheapest one. If (when) it fails, I replace it with one that is better along the metric that the original failed in.

For hobbies, they say "buy once, cry once", but there are so many ways to be unhappy! I won't limit myself! I say buy all, cry all, and learn all the different ways to cry. I don't ski, but for the analogy, I'd try short ones, long ones, cross country ones, racing ones, red ones, blue ones, etc and then only buy really nice ones once I understand exactly what the nice ones do that the others don't. There's a good chance that I'll learn I like skis more than I like skiing, and that's okay.