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No problems yet...

Updates work just fine and are only performed at reasonable intervals

Sure. The approach seems like it works for you (so far), and sounds like it worked out well for whoever got money out of you.

But, please don't encourage others to put themselves at risk. aka fall for a scam on Ebay

I disagree, but I admit it is risky.

the keys seem to be about $2

you could get scammed or have your key deactivated a hundred times and still be ahead

That's assuming there aren't backdoors in the software. Not a safe bet to make.

At least, not without (at a minimum) having the SHA256 (or better) checksum of the ISO match that of the MSDN equivalent download.

MS provide the digests on MSDN if you have a login

and there's plenty of dumps of them kicking around if you don't

Most are MSDN license which will invalided and deactivated sooner than later.