This may seem a little counter-intuitive, but does this make sense? When voting, fill out the ballot by...
#1: Voting your heart. Put the person who may not be a 'top' candidate and whom you don't think is actually going to win, but who deserves a shout-out because of all the great work they've done in the community over the years. There are a number of candidates on the ballot who fit this description.
#2: Voting your head. Put the person you'd be happiest with and whom you think has a real chance of winning thanks to endorsements, money, organization, and name recognition, but who may need that extra push over the other 'top' contenders to make it. When your #1 person gets eliminated, then your #2 gets your vote.
#3: Voting your ass. Well, cover your ass, at least, with your #3 vote. This person ought to be one of the 'top' candidates, but someone you're not totally on-board with for one reason or another. Maybe they're inexperienced, have a skeleton or two in their closets, or they just haven't lit a fire in your heart for some reason. They're the best of the rest in your mind, and hopefully would be only slightly objectionable if they were to be elected, but you could deal with it.