I've been paying for singing tuition for the last 6 months. I only took it up so I could do a half decent job at backing vocals in the covers band, but I'm quite enjoying it now, and I'm even singing in a singers concert in a week! It's cool though, because you need very little gear to take it up as a hobby. But the money I spend every fortnight for a lesson I feel is well spent.
Hence, I'm thinking of taking up guitar lessons again, if I can find a good teacher in Wellington... There's something about putting your money towards tutelage that's rewarding for me. Especially for something like guitar, where it becomes a life-long skill. Plus, I'm forced to sit and practice weekly and be a good "student" (YMMV).
Good/cool gear can go a long way to making great music though. Don't discount it as a fools errand. It depends on the type of music too though. A blues guitarist might sound great with a good sounding SS amp and a strat, but a progressive rock player may need a bit more at their disposal, but it certainly doesn't need to be wow/rare/uber boutique.
Mind you, strats all sound the same no matter what they're going through
Ever tried to get a big rock sound from a cheap LP in to a cheap amp? Different story. That's certainly not going to inspire me to play.