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Went well for me too... I have a more detailed post within another thread about my experience and some of the major and minor improvements I saw here and there in the OS.
There are listings online of what 3rd party apps work or don't work in WM2003, I would definitely recommend consulting one of those lists just to get an idea of where you would stand with the software you are using now. Aside from that, if most or all of your applications would be supported then I would say go for it. IE is much faster, Activesync is many times faster than before, and personally I haven't really experienced any of the problems users have been reporting. Just make sure that you follow the instructions very carefully.
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