I finally got around to buying an iPod about six months ago. Of course, shortly afterwards, Apple doubled the memory, so if I'd waited a couple of months, I'd have been able to get a 4MB nano for the same price as I paid for my 2MB version.
I found my daily commute to work was made more bearable. I was also struck by the number of fellow commuters I saw using an MP3 player or similar. Before I got the iPod I only noticed the occasional person whose earphones leaked their music to the whole train carriage. Now I saw that roughly half those travelling with me seemed to have earphones as well.
My musical tastes were set some thirty-odd years ago - think Led Zeppelin; Ten Years After; Emerson, Lake and Palmer - and they don't get much airplay these days. I am really enjoying hearing again the music of my youth.
One tip - I suggest you invest in a pair of headphones instread of the "bud" type earphones supplied by Apple. While the sound seemed not too bad, when I tried a decent pair I noticed a tremendous difference. Apart from a much less "tinny" sound, quiet passages were still audible. Before, I found myself checking that the iPod was working properly as I could hear nothing at all.