We are having a few similar issues with our PTO and school relations. However, our school Director is probably the opposite of yours, she is very nice and agreeable, but sometimes it detracts from real progress being made.
I think we did a good job of "winning over" the teachers and director by starting the year off with a teacher appreciation luncheon around Thanksgiving. (It was so successful, we have another one planned for teacher appreciation week in May.) It takes some organizing, but we posted sign-up sheets requesting various items from the parents: entrees, drinks, desserts, paper plates, tableclothes, favors for the teachers, and volunteers for set-up, clean-up, and some parents to make "reminder" phone calls.
You could also try to work with your principal's style. We invite our director to our meetings and present new ideas to her by stopping by the office and saying, "This parent had a great idea, it goes like this, what do you think?" She likes that we check with her. We had one instance when we spent a lot of time on a fundraiser that involved a friendly competition between classes to see who had the most participation. After painstakenly writing class numbers on hundreds of flyers, the director told us that she and the teachers did not feel comfortable with preschoolers "competing". Had we given more notice of how the fundraiser was set up and gotten feedback, we would have saved ourselves some trouble.
We have a very old school but they have not had a active PTO in over 15 years. We have myself and one other lady who are very passionate about helping. We have had a lot of road blocks. First off the Principle is not easy to deal with. She has to control everything that happens. While I understand this is her school. She does tend to go over board. EX. We were thinking about doing a 5th grade picnic since it is their last year here so we talked to the two 5th grade teachers in passing just to see if they thought it was a good idea. It got back to out principle and she was mad that we did not talk to her first. All we were doing was trying to form an idea and have proper information gathered so we could present it to her the right way. One other EX. the PFO money we make, she controls and uses with out asking us or even letting us know she is using it. So we have issues there lol.
Other issues are we are a below poverty area and over 85% of our children are on public assistance. Most of our parents do not hold jobs and when we have a meeting or family night or ANYTHING we are lucky to get 5 or 6 children show up with a parent. We always send fliers home and always have the food and drinks and make the event happy and uplifting. But our parents just do not make the effort to be involved.
The two of us are trying so hard to get the PTO off and running and really do not know how to go about that. Between the lack of response from the parents and the way the principle treats us we are lossing our want to help.