I have a Mexican Strat (that I affectionately nicknamed Puddin', cause of the color) that I got in...1996, I think. To be a Taco Strat that thing has a great sound and plays like a dream. The tuning keys suck, though. It's starting to come out of tune easily and I think that may be why. So I'm gonna replace'em with some better ones.
I have an Epiphone PR5-E acoustic/electric. I like that one okay, I suppose. One of these days I'm gonna own some kind of Martin. But for as much as I play acoustic (only in church, and rarely at that) the Epi works fine.
Christmas of 2001 I got an American Telecaster. Great sound and really fast neck on this one. Especially great if you like twang (I do). My grandpa has a Les Paul that I borrow a lot.
Easiest song: Hmm, the very first thing I learned was a generic 50s progression (G Em C D).
Hardest song: Though I've been playing for lots of years, I still suck. Plus, I have no patience to sit down and learn a complete song.

The two songs that have given me the most problems, though, are "Lenny" and "Riviera Paradise" by Stevie Ray Vaughan.