None of my Smart Playlists are syncing properly (normal playlists sync fine).
It DOES sync to the number of songs I want.
However:
Recently Added just puts on the first 100 songs in alphabetical order by artist.
Recently Played appears to work fine.
Most Often is totally random.
THE WEIRDEST PART:
In iTunes, when i click "Brandon's iPhone" and click the playlists, it shows the proper songs. They just don't list properly inside the phone.
I'm seeing exactly the same thing on my touch iPod. It has been driving me nuts ever since updating to 1.1.1. (Maybe before that and I just didn't notice.)
I have not figured out a workaround beyond doing a select-all in the smart playlist, making a non-smart playlist from the selection, then syncing that (non-smart) playlist instead.