What is the benefit of buying registrations as a group?

Simplicity. One person can handle the transaction.

If you're entering the housing lottery, there is the disadvantage of only getting a single entry rather than one for each badge purchaser.

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Alec Usticke, Fans of Gen Con Facebook Group

Great, thanks.

@gospeedbarry - In addition to what austicke mentioned, though, if you buy as a group one person can book 1 room for every 2 badges purchased through their account - so, if you have a bigger group, you *might* increase the chances of getting your group into the same hotel at the cost of losing another entry into the housing lottery (which just controls where you are in the line).