Dave, Jessica, Bob Rosie and Shawna should vote. Have they? Then you should be able to tell Dave that the votes are in. When he unlocks the box you can steal all votes except for the person you want to win.
If you're almost at level 30 I recommend considering waiting, then possibly take the "almost perfect" perk which places all S.P.E.C.I.A.L. to 9. Then you cat take the Bobblehead to get to 10.