As for the issue presented by the OP, the reason they do not allow you to choose more than one roommate is so that a whole group of people doesn't get a "free pass" into Keyes. Especially if one person has like a 12 average, and they might be guaranteed a spot in Keyes, they don't want you being able to bring ALL of your friends along for the ride. Similarly, if one person wins the lottery and gets Keyes, they don't want them bringing all their friends in that way either.
The suggestion Kathy2 made regarding the circular roommate selection doesn't work, because if I remember correctly, for the matching to work, each person in the pair has to list the other person as their requested roommate.
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