To be frank, that is a stupid plan. Combatting priacy is one thing. But doing so to prevent people from updating the bootleg OS is another. Plus, such things will never work either.

Let's say Legit User goes to the MS site to download updates to have them manually installed. That file is downloaded to that person's HD. The file sits and can be sent to Bootleg User, who has a bootleg copy. Now just how in the friggin' world are they gonna prevent people from doing THAT? It doesn't make any sense!