I agree that there comes a time when one should consider stepping up when the time is right.
The one and only time I did a night-after-night "tour," I actually played keys and bass. We did an 11-week tour where we played 6 nights a week in a different spot every night. On weeks where we stayed at a camp, we played at least twice a day. None of this counts rehearsal time. If you are like me, you will be amazed at how fast you stop caring about finishes and cool little accessories on whatever gear you are playing. All you care about after about a week or so is that it works, and that it works well night after night. The group I played with provided a pretty nice keyboard and a P-bass for me to play with. They were decent-quality instruments because the last thing you need is something breaking down whenever you're playing out in BFE about 3 hours from anything remotely resembling a music store.
For probably the first 10 years of me playing music, my friends and I always play crap gear. I had (and still have) a set of Tama Rockstars from the early 1990s, and I probably had the nicest instrument that anyone else had at the time. They all played off-brand guitars, crummy amps, and sang through a half-blown PA system. Granted, we had an absolute blast doing so, but good gosh our gear was horrid.
There's something really nice about showing up to play somewhere knowing that my gear is going to sound pretty darn good anywhere I go and there's a low likelihood of anything breaking. I like to concentrate on my playing as opposed to worrying about something not working like it should.