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Why do you think you can only install DLC on one machine when you can instal the game on any machine?
Or does skyrim have a launcher of some sort that has options?
For Skyrim, make sure they appear under the data files option in the launcher and that they are ticked as enabled.
Accounts are not machines. Steam doesn't even handle DLCs properly when multiple accounts are involved, but generally, they are meant to be owned by the same account that owns the base game.
It's on his account.
When did you buy the DLC and when did you last check that it wasn't working?