I can't vote for Jefferson Smith for mayor because he is a total fuckup. I can't vote for Charlie Hales because he's a lying son of a bitch. At this point, any alternative sounds good. Who can I write in that has the best chance of winning?
Well, Michael, I must say I've got a few ideas. Modesty forbids my sharing them with you.*
As recently as two weeks ago, I probably would have urged you not to waste your vote on some quixotic write-in campaign. However, it's starting to seem (ahem) like the Portland mayor's race isn't going to be all that close. A few wackos writing in "Adolf Shitler" or "Boner McDoucheathon" aren't likely to swing it one way or the other, so knock yourself out.
That said, if your criterion is electoral viability, I'm afraid you're pretty well hosed. My research turned up just eight successful write-in candidates in municipal elections ever, anywhere (and that's counting the mayor of Talkeetna, Alaska, who is an actual cat).
Furthermore, I found exactly zero examples of people (or other mammals) winning as write-ins without an active campaign. Mr. McDoucheathon may have fascinating ideas about the gold standard, but unless he gets out on the stump PDQ he's going to spend yet another Election Eve scraping dried chili off the nacho machine and dreaming of what might have been.
Still undeterred? Then pick someone whose name is easy to remember and spell, like "Michael Jackson," or "Free Beer." And don't forget to color in the bubble next to the write-in blank—your vote won't count if you don't. Frankly, as a write-in, it won't count anyway, but at least you'll force the bastards to write it down.
*This is a joke. Please do not elect me mayor. Thank you.