Once Windows is done upgrading, you can go to the System control panel and change the activation key to your MSDN one, and activate with that. The only solution I've found is to use a regular upgrade or retail key (if you have any from other installations) to initiate the upgrade process, but choose not to activate automatically. However, as mentioned, you cannot do an anytime upgrade with an MSDN key. With some MSDN keys (it's unclear why this occurs with some and not others), you may be informed that an upgrade installation can only be done with Windows Anytime Upgrade, not from the DVD. What "riskiness" are you referring to? If you use genuine media with a genuine key from MSDN, and do an upgrade install, there shouldn't be any significant risk. You can still perform an upgrade installation, it will just be running from the DVD you burn. If you have MSDN access, you should be able to download a legit ISO from Microsoft directly. You have to find regular installation media. You can't use an MSDN key for an anytime upgrade.
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