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Well, the one reason why we advise people against using Fedora as a server is because we want them to stay up to date, and this entails frequent updates. Latest packages are good, since they will have bug fixes, which can be security related or otherwise.

I can't say how any Fedora version compares to a Windows server. I wonder how one would test this.

About upgrades: upgrading using yum works, if you know what you're doing. However, the number of changes between F14 and a current fedora release are too many, and the chances of the upgrade going smoothly, too small. If you have the time, I'd suggest a data backup and a CentOS/Scientific/RHEL install.