Well I hafta admit,
I never did the iPod thing. In my mind, there were tons of competitive products with similar or more storage for a fraction of the price (and usually, more features like FM radio). So my first iPod was my iPhone 4 32GB I got in 2010!
That said, I really do like the accessory market, compatibility and integration with everything, and how much better it plays with iTunes, et al. Definitely the best mp3 player out there, but it took them adding a smartphone into it to finally sell me. That kind of a feature is hard to look past 😎