I started with the Motorola MPx200 back in 2003. It ran Windows Smartphone 2003. The best thing is it wa a beautiful device. Pearl blue and piano black...
Motorola MPx200
Then I went to the "MPx" (or MPx300). This was strange because the phone was only available from eBAY and a couple of private sources. It was never officially launched. It's the only time I've anything like that happen with a phone. The dual-hinge was the jizz.
After that I got the commercialy available Motorola MPx220. This one was a huge bummer. Soooo many problems with it. But it the first WinMo phone I had that had a ROM upgrade come out for it...
...and so on and so on. After that I took the usual path...you can see it in my sig.