My hunch is that indivduals get absolutely hooked on sailing when they sail a small boat by themselves. They make mistakes, ask questions, get the boat going well, get their head out of the boat and then enjoy the beauty of moving on the water with just wind and waves. Once hooked, you just have to go sailing and it's just easier if you drive! Its just not the same experience with one or in the case of a big boat with several others on board. Until you have the total responsiblity for going out and bringing the boat home you won't have a sense of sailing.
If you don't have the passion to just "go sailing"... the hassle factor of getting a cat into the water will stop you every time. I don't think we develop many women skippers because physically a cat is a pain in the butt on the beach. If the boat is just too much on the beach for you as an individual, I think you will be stopped. I don't know of too many men or women who want to be dependent on someone else for their well being. Bottom line... we need small, light fun performance boats for women and kids to sail independently. I think you also need to start or migrate to a boat that you can also sail socially and not just race.
The overwhelming participation of women racers in events like the Rolex demonstrate that quite a few women are very competive, enjoy putting together teams and do go racing. Even at the level, the majority of women sailors are crew's and not helms. (3 to 4 man teams)
I also think that a critical element is to have sailing yacht clubs which provide the support and expertise for a novice women helm to draw on AND a boat that they she can manage on her own. Notice that women race Europe dinghy's and not lasers at the olympic level... If you have ever seen a europe you would not have any doubts as to why.
Take Care
Mark