Yup, same here.
In July 2008, I bought an iPod touch from a guy off Craigslist. His son bought an iMac and got a first gen iPod touch he didn't need because he already owned an iPhone.
Then I started watching videos on YouTube about jailbreaking. After about 4 days in vanilla form, I decided to JB it and was astonished by its potential. I loved it! This was before the App Store had anything useful yet. I even streamed my videos and online channels using OrbLive. Long before Air Video. Summer of 2008 feels like yesterday, but in the tech world, feels like ages ago too.
Carried the N82 and iPod touch, but also hated carrying two devices. My mom wasn't into her iPhone that was handed to her by my brother because the ringer volume was too low even at max. Kept missing calls. In Nov of that same year, she went to Paris and let me use it. I JB it, and realized that I wanted it. When she returned from her trip, she just gave it to me and got herself a Motorola Z9. Signed a new AT&T contract and then used the 2G for 8 months as my primary before the data got cut off.
And around 2008, I hated Apple. But the respect and infatuation for Apple again started from the iPod touch... No contracts and a jailbreak community that saw the unlimited apps potential where you can turn it into almost anything YOU want it to be. I will keep my iP4 in vanilla form though. I got so spoiled by apps before, but realized I don't really use or NEED many of them. I am going for the minimalist approach now.