I say it depends. In most cases, it kinda bugs me. I won't completely shun the idea, since sometimes it works (I've seen a damn good gender-bender of Oerba Yun Fang from FFXIII)
Or maybe some people just can't pull off a crossplay?
Aren't most gender-benders "female-version-of-whoever"? (that's technically the part that bugs me, but then again, I am a crossplayer)
Anime North 2012: Shadow the Hedgehog (SA2)
Halloween 2012: Roxas (KH2)
Anime North 2013: Tweedle Dee (Alice in the country of hearts)