I play electric guitar, and have been doing so for just under two years. Quick rig list:
1. PRS SE Custom 24
2. Line 6 Pod HD400 (love this thing. Line 6 modellers are good, which makes me wonder why the amps suck so much)
3. A 30 watt tube amp I built myself. Used a guide to help me along of course.
I also have an Epiphone Les Paul Special II (eh) and a Roland Micro Cube (decent for what it does). When I first started playing, I was into Metallica, U2, R.E.M., and a few others. I started out playing the easiest stuff, and then I just sort of built on that. Unfortunately, while I can play a lot of stuff off a tab, my music knowledge is crap.
My first time playing live was actually somewhat recently. It was a smallish setting, but there was a small music thing downtown where I live. What I ended up doing was (sorta) playing three songs by Animals as Leaders. In order, they were "Soraya", "On Impulse", and "Point to Point". By sorta, I mean that I could play the main parts on all of them, but the solos in Soraya and On Impulse are simply beyond me, so I made my own solos that fit the song but were less complex. This was where I wish I had some music know-how, as I could either improvise my way out of it or at least not spend so much damn time writing the things. On top of that, I had someone I know isolate the drum tracks, and then had him slow it down to like ~85 percent of the original tempo. In the end, I think it helped, and people still liked it.
I'd have to say the first half of Soraya was a roadwreck. Nerves got to me, and I couldn't really get into a rhythm. At one point I completely stopped and just listened to the drum track. After a bit, I was in business. On Impulse went really well, and I was proud of the solo. Point to Point was something to close up on, and it went pretty well too, except for me screwing up a chord on the slow ending. Overall, I think people really liked the change of pace from the power chord-heavy traditional rock (which we had lots of that day) to something a bit more jazzy.