1st-gen iPod. I had to use hacks like XPlay to use it with my VAIO laptop. And once in a while that would lead to a corrupt file system on the iPod and I had to find someone with a Mac to do a restore.
Talk about a halo effect...
I still remember the day my dad came home with an Apple //c for my brothers and me. The next day, one of my buddies from school let me borrow his Ultima IV on 5.25" floppies and it took us about a year to complete. The funniest feature on this was the button that let you switch the keyboard layout from QWERTY to Dvorak.
I'm pretty sure it's still functional and sitting in my parents' basement.
I first got a 5th Gen iPod Video in December of 2006. It got stolen outta my car about 5 weeks later. Then, I bought my first iPhone in November of 2008. Then bought a iPhone 4 on launch day in 2010. After that it was all down hill and went on an Apple spending spree. 2x Apple TV 2nd gen. Apple Airport Express. Another iPhone 4. Then a MacBook Pro 15" on the 2011 launch date, then sold my Black iPhone 4 and bought a white one. And just got my gf a iMac 21".
They done got me for mah paper....
My first apple product was a Performa 630CD back when I was in elementary school. I remember it came with a booklet of cd's and I would use ClarisWorks and play wacky jack's all the time. It was also pretty hard to find Mac sw back then, everything was windows. Kind of came full circle. Mac->PC-> Mac