I still remember the first time I saw an iPhone in real life. I was waiting for a table at Texas Roadhouse with my girlfriend at the time, Janalyn, and the two girls sitting next to me were texting hardcore; one of them was on an iPhone 2G. It looked gorgeous, and I knew that I had to have one.
I got an iPhone 2G with my tax refund in February of 2008, and I've had every iPhone since then.
Jailbreaking only makes iPhone better!
This jailbreak was fairly straightforward. After updating iTunes, and saving everything that I needed to save from my phone (just in case), I upgraded to 4.1 from 4.0.1 as normal through iTunes. After that, I followed the instructions from modmyi.com. The jailbreaking tool is called limera1n, and it is completely free (geohot does accept donations though, and a donation is well worth it).
After the jailbreak was complete, I backed up my SHSH blobs using TinyUmbrella. Without getting too technical (because I'm not sure that I fully understand it myself!), this allows you to restore your iOS back to the backed up version if Apple releases a new version. For example, if Apple releases iOS 4.2, then they will stop approving iOS 4.1 for restores; you need the SHSH data to trick iTunes into thinking that Apple approved the 4.1 software file.