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HTC/iMate Jamin. To be fair, the skins HTC are making for Winmo5/6 make it a much more enjoyable experience than the version I had - which was buggy, crashed every day (I think my record was 5 crashes in one day) and was a generally a bit of a nightmare.
I had a blackberry after that, which was ok, but the camera & media consumption options were crap so I got an iPhone which is still going strong after 2 years.
I had a O2 XDA ( HTC Hermes) with WinMo and I have to say compared to Andriod/Iphone, WinMo is considerably clunky. But I got my phone much before Iphone came out so WinMo was in a good position to improve but they havent caught up.
I now have a Samsung Galaxy with Andriod and it is definitely on par with iPhone on the user experience level. The stakes in smart phone technology are going up in massive steps and I only hope Google can keep up with Apple.