Looking for help buying a Guitar.

I've played some inexpensive Ibanezs that played pretty good, so if you can get one for cheap, why not. You don't want to get something too good to learn on, because the easier a guitar is to play, the easier it is to become lazy and develop bad habits in your important development phase. A good starter amp would be a small Crate {or at least, that was a good starter amp back when I was learning to play}. If not an Ibanez, then look at some of the less expensive Epiphones or a Squire. I wouldn't play an Epiphone or Squire, but that's just because I've been playing for a while and have a Gibson Les Paul Studio {pretty much one of the low end Les Paul models, but perfect for my level of skill and still a great guitar}.

You could probably find some good websites to look at, or spend five bucks on a good chord book, which is what I did. You might want to either get a handful of private lessons to teach you the basics, like tuning it, basic chords, and very basic theory, or if you have friends who play, ask them to show you a few things.

Jam it back in, in the dark.

I've got a DS-1 that I was extremely pleased with back when I had a shit guitar and a 15 watt Crate amp. You've most likely got a better guitar than I had, so you'd probably be pretty pleased with a Boss pedal. Since you're obviously not going to be able to really test out a pedal yourself, go to a guitar shop with a friend who can play and have him test out a few pedals for you, on a guitar and amp similar to what you have, that way you can get an idea of what kind of sound you can expect from the pedal. If you don't have a friend who can do that for you, in my experience many of the salespeople at guitar shops are cool dudes and chicks and would help you in the same way.

Also, as far as the pain on your fingers goes, practice a lot and your fingertips get pretty tough {callouses are your friend until one peels off and your fingertip is so sensitive that you can literally FEEL the air around it even when your finger is stationary}.

There's nowhere I can't reach.