no all you need to do is flash a gingerbread rom and you are updated. no need to any rooting any more. try mikg2.56. it is a gingerbread rom with sense 2.1 and sense 3.0 built in. it is super fast and very stable. and it is all stock with no theme. check it out in the roms/kernel sticky.
You shouldn't have to reroot. as long as you have S-OFF you are good to go. As far as updating not sure what you want to update? if you have a Stock Rom DO NOT UPDATE WITH AN OTA. Get and Updated ROM like MikG. Most of the ROMS will have the updates available. In fact you want to uncheck the Check for Updates on your ROM so it doesn't updated it.
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