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Perhaps. I have not tried this directly. I have gone from FC1 > FC2 > FC3 using yum via ssh access. I did this on two production boxes at ServerBeach and consider myself *darn* lucky something didn't break. With those upgrades, the standard "there are somethings that only anaconda can do" applied, but I guess I wasn't using the packages that really mattered (not big on X on web servers). I would try it on a test system first, perhaps grab a trial version of VMWare and try to recreate your setup and upgrade. Report back with the news. I can already see gcc4 giving issues, but you could get lucky.
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