recording using a computer? need musician and computer geek!

Hey all,
I'm a chick (that's out there for the one looking for other girls) and I've been playing for almost a year.  I also play the piano although I don't play either very well.
Anyhow, this is what I would like to do.  I use to use Midi Orchestrator for my piano.  I would plug it in and record tracks, play around with drum beats, it was fun.

But now I want to do this with my guitar.  Do you have any advice?

I would like to ultimately have something that will record both my guitar and my piano.  My piano has midi cables, but I know now that I can get midi to USB cables for that.  but what do I do with the guitar?  And what software will handle both? What are my options? I don't want anything too technical and expensive because I am not a performer, just a lover of music.

My guitar has no pickups.  Would it be easier to buy a guitar that has pickups?
So i am looking for the computer geek and the music geek to help me out.  I will go to Sam ash or guitar center, etc, but I wanted to go in with some knowledge.

Thanks in advance!