Although I bought the WM5.0 upgrade for my Dell Axim X50v, I am still running WM 2003SE, mainly due to some incompatibility issues with tools I cannot live without (such as CardExportII for direct file access via USB. I know that Microsoft is working on WM 5.0 AKU 2.0 which supposedly includes true "push" e-mail support and tons of bugfixes.
While there is no guarantee that the upgrade will be available for all current Pocket PC devices, chances are that if you buy a WM 5.0 device now the upgrade to AKU 2.0 will more readily available than if you buy a WM 2003 SE device.
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