Oh yes, the iPod is the shiznit.  I had a Rio 500 for a number of years with 128 megs of ram and got my iPod about 6 months ago. 

I do recommend, however, immediately jettisoning the crap MusicMatch software and using these tools:

• EphPod for the quick and dirty work: Add a song, edit IP3 tags, adding Outlook Calendar appointments, vCard Contacts, text files, etc.
• MoodLogic and DeviceLink are the best thing to happen to MP3s since Napster.  Of course, I don't share music anymore, but I do rip the hell out of my 500+ CD collection.  MoodLogic is worth the money just for it's song identification capabilities.  It fixed the file names on at LEAST 1000 of my songs, including what # it is on the CD, who the artist is, etc.  Plus, it creates "Mood Mixes" in the iPod automatically.  Coincidentally, the core of it's iPod compatibility is...EphPod.
• Then, just for kicks, use Muse.NET to listen to your 20 gigs of music, legally, from work with .NET and Web Services.  There are lots of sample applications (many in .NET) to exploit their API, and exploit the programmaticalshipfulness of your music.

Now, if I had only waited, I could have had a 20 gig iPod for the same price...