I got a gen 1 iPod, its 7 year old & still working. Apple products quite lasting : )
I'm considering getting an iPod touch or Iphone because its small & will allow me to check emails when I travel. Many countries now have Wi Fi hot spots.
I've got a Hi Fi system equipped with Monitor Audio & Jamo Speakers which I think is better than Bose & sometimes I hook up my iPod for the Hi Fi experience. With the iPod, I can access my music collection faster than my CD collection.
I don't know anyone who regretted getting their Apple products. Could be because they are not impulse buyers. They are not buying an Apple product because its some kind of status symbol but because of the user friendliness of the products.
Its a pity that Singtel has been chosen to distribute the iPhone. They are out to ketuk their customers. I may pick one up in HK where its suppose cheaper.
I regretted because iPod restricted my FREEDOM to copy songs, podcasts, audiobooks etc... to and from computer without using the bloatware iTunes (comes with mobile stuffs etc.. even if you don't use a iPhone).
Presently, I bought a Nokia symbian phone for the first time. It came with GPS, WiFi, Podcast, Audio Books, Radio, MP3 Player, Camera, Network Access, Push Mail, Oxford Dictionary with Audio, Wikipedia, Document Editing, PDF, Book Reader, Picture Uploading, Sync with Server and Calendar. One up for Nokia!
My iPod relegate to the reservist unit now. I really appreciate the FREEDOM to move all my data without any restrictions at all. don't think I will have any interest in IPod again. BTW I owned 3 iPods... and now I know what I'm missing after using Nokia.