Keep in mind that most of the traffic now is on the forums (traffic exploded after adding it). There's already a sticky saying to read the FAQ...we could add a second sticky with a few basic questions/answers, but I'm not sure how much good it would do.
if a user is too lazy to update or to read the FAQ, i think a reminder wouldnt help.
Well I never went on the forums but read wine-users only via the mailing list, but apparently I'm an exception here ;)