I have been using Mac's since January 2003.
My first Mac was an G3 iMac "Snow", which I loved! I have to say, the main reason I wanted to 'swtich' was because of the Operating System. Things like 'protected memory' and 'never crashes' caught my attention when I was 15 years old. The iMac came preinstalled with Jaguar (10.2) and Mac OS 9.2.2! I was able to select what OS I wanted to boot into. I could also launch Classic applications inside Mac OS X.
I used the iMac for roughly 2 years. I sold it on eBay and added extra money to purchase an eMac. The eMac was just over double the speed and it was a G4 processor! It has had a 2" bigger screen, which was a lot crisper than the iMac. The eMac was very loud. My parents could not get to sleep at night in the room next door due to the 'droning' from the eMac (which of course was the fan). Also, when closing the CD drive, the plastic section that covered it used to make a loud "clunk!". I did love the machine however, but I only used it for a year.
After using the eMac for a year, again, I sold it on eBay and added money and bought an iBook G4. My two prior machines had been the cheapest entry level Mac's at the time. I was so proud purchasing an iBook G4 - 14" model with Superdrive! I loved the iBook. It was built really well. The only thing that niggled me was the resolution - 1024 x 768. This was my first laptop, and I used the iBook G4 until January of this year (I had it for 2 years). I knew at this point I could never go back to a desktop, considering how much freedom a laptop gave me - especially having a wireless network in the house.
Due to having the iBook two years, and the release of the intel processors, I felt an upgrade to a MacBook would give me huge benefits (iSight, MagSafe, faster, higher resolution, smaller). I purchased the entry level MacBook. I have problems with 3 consecutive MacBook's in a row, however my fourth MacBook in the space of a week seemed to work fine. A month or two later, updated MacBook's were released with the Penryn processors. I thought that considering I had some extra money, by selling my current MacBook and adding roughly £100, I could get a far superior computer. So I sold it on eBay and bought the middle of the line white MacBook which had a 400Mhz faster processor.
Due to my disappointment in the quality and construction of the MacBook (all the models I had did not feel constructed well - no where near the quality of the iBook), I decided to sell my MacBook on eBay last week, and I have used the funds from the sale and some of my own money to purchase a MacBook Pro (entry level) which I am currently using just now. It is the first time I've had one of Apple's pro machines, and I love it. I know that the MacBook Pro will satisfy me longer than the MacBook I had previously. That is part of the reason why I opted to go for the Pro. It is far superior in quality.
A little more in-depth than was probably required, but there is my story on when I became a switcher, and all the consecutive Apple computers I've had since then.