I feel that I need to reply as a principal who tries to work closely with my parent group. The answer is communication. If the principal isn't a regular attender at the PTO meetings, they need the professional courtesy of being informed of ideas that the PTO is generating for events, fundraising, etc. BEFORE they begin planning them. I have a very good relationship with my PTO because I attend most of the meetings, but if I didn't I would want to be consulted prior to planning things because while the events may be well meaning, they may make more work for teachers and school staff and if those people aren't informed "up front" it can generate angst and the principal usually gets to deal with that. Also, there are liability issues that need to be considered and sometimes the parents' view of how things could go butts up against district policies and procedures. Communicate, communicate, communicate.
Sounds like you really want what's best for the kids at your school. Why didn't the principal want a PTO? It's hard to comment on the situation without knowing more about your conversation with him and what his objectives and objections are. The bottom line is that you have to figure out a way to work with the principal.
I am having trouble with our principal. At first he wanted a PTO, then he didn't. So I went out on my own and formed an independent outside group that donates all proceeds, etc to the school. I am also the coordinator on certain fundraisers. Every time I try to do something through the school he has an issue with it. I, by myself, acquired almost $6000 in donations recently and he didn't even say thank you.