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I'm no expert, but if I'm hearing you correctly on your second question, only use ROM updates specifically for your device. Get the Dell authorized one and go to town. Anything else will void your warranty (if you have one,) and potientially turn your device into a $400.oo paper weight.
As far as practicality, I never used WM5 so I can't answer you there. From what I have heard though that it does have some issues with third party software, so keep that in mind when considering, or search the boards here and get the skinny from actual users. Either way good luck.
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