I started with iphone 1.0. Originally, I wanted a pda-phone so I had saved up money already to buy an ipod and blackberry; I hadn't pulled the trigger, because I thought the bb was hideous. Unfortunately for rim, when Jobs showed off the iphone, they were a distant memory.
The news had me obsessed and wanting more information about this new device. During the time I waited for the release, I went looking for information on the iphone and came across macrumors.
The phone was pretty much everything I wanted. Using the maps app was so great when I went on vacation in NYC. Obviously, I loved having my ipod and phone in one device; there was no issue of separate devices. My friends and I loved being able to google things when we had a discussion about something. In fact, my friends with blackberries were asking me to google things on my phone, even though they could've technically used theirs. When I asked why, they told me it was a bitch using the internet on their phones. Until they told me that, I didn't realize the internet experience for other phones was that different. When they showed their internet to me, I was repulsed and glad I lucked out.
The only things that marred the experience were the lack of custom ringtones and the reception from the metal body. The former was easily taken care of thanks to the hackers who popped up. Luckily, it was also pretty easy.
As for the reception, it was somewhat blocked due to the metal casing, so I always roll my eyes when some fool suggests the next iphone should be all metal.
Interestingly, when my dell died, I was looking at these computers pre-loaded with vista with disgust. Looking at the mac, I decided that anyone who could bring out a phone this awesome would probably also give me a good computing experience. It turned out I was right and have been enjoying my apple experience ever since.