It's a little odd to require him to pay dues -- but the dues argument has its own thread on this message board.

Yes. I've never had a principal not join.

I've been involved with my kids' middle school for several years. I've realized that for the past 3 years, the current principal has never "officially" joined the PTO, meaning he has never filled out a membership form or paid dues. Quite a few of his staff join, both his Assistant Principals join, and the faculty rep joins. According to the by-laws, he is the Executive VP of the board. And the by-laws state that you can't be on the board without being a member, although he is technically an ad-hoc non-voting board member. Still, shouldn't he join the PTO?