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.