Sounding good with the gear you have
There's a point at which all the gear-flipping in the world isn't going to help your playing. However, ...
For me there was a period where I went through a lot of gear trying to figure out what really worked for me. I spent a lot of time messing around with gear that touted "flexibility" (you know the kind: digital modelling amps, channel-switching amps, rack gear, effects, guitars with a bazillion switching options, etc.) before I discovered the joy of simple gear.
Now my rig is normally just a guitar straight into an amp. I have, as a result, learned a lot about touch and dynamics. I never would have reached this point in my playing had I stuck with the more complex rigs; they work against development of touch and dynamics by having extra knobs and buttons as a (poor) substitute for being responsive to the player. Therefore I'm really glad that I didn't just "shut up and play" at the outset.
Although I can now get "my sound" out of just about any guitar and amp (I've been amusing myself lately by going to shops and trying out inexpensive gear), there are certain kinds of amps and guitars that - to me - seem to work better. It's not so much a matter of sound as it is a matter of comfort and familiarity.
That said, the core of my rig has been quite stable for a while now. I finished selling off most of my less-used gear a couple of years ago, and have acquired very little since then. I have a "policy" of selling any gear that sits unused for a year or is otherwise just a bad fit. (It happens... It's amazing how quickly I can get tired of something that sounded good in the store, particulary w.r.t. effects.)
Since I've stopped paying so much attention to my guitar rig, my guitar playing has greatly improved thanks to the time I've been able to commit to study and practice. However, I've only been able to do that since I've become really comfortable playing the gear I now have. I'm finally able to hear my playing without thinking about the tone or the feel of the instrument.