Two-pass encoding for .ogv transcodes with ffmpeg2theora are currently disabled; it was briefly re-enabled but turned out to be too flaky (T109608) with our current ffmpeg2theora, which is probably when it was disabled to begin with. ;)
Since I can't reproduce the encoding failures with updated ffmpeg2theora versions on Trusty in Vagrant, I think it should be safe to turn it back on after updating the video scalers.