Re: Does tone really matter?
Have to break up into a live vs recording comparison. Live tone doesn't need to be perfect and most people in the audience will only be able to distinguish a clean tone and a distorted tone, with maybe a bluesy breakup tone in there. Other than that, the room acoustics, people cheering/clapping, and general audience noise is going to cover anything else up. You don't really need to spend too much time trying to get that perfect tone as good enough (unless you're doing a dvd or something) will be just fine. I've had people tell me my tone was pro-tone (quite flattering) but have never had someone tell me my tone, rather than my playing, needed work.
Recorded tone is different and, IMO, does require a bit more meticulousness. Something recorded is going to be listened to more than 1 time and is going to be scrutinized. You want your best sounds coming out on that. It's more than just your rig, since what you record with influences things, but, at least for me, I want it to sound how I want it to sound rather than just good enough. In that sense, I do think it pays dividends to tweak and get the best out of whatever gear you're using, while recognizing that some gear is just not designed to get a certain kind of tone. It's not worth completely obsessing over and buying tones of gear to use only when you want one particular sound, but it's recognizing that if you really want a particular sound, sometimes you have to bite the bullet and get that particular piece of gear.
Even if you don't intend to produce your music, I find that I obsess over tone when recording way more than live because I want it to sound as close to what I hear in my head as I can get. On stage, I'm just worried about not flubbing and being loud/eq'd right with the rest of the band.