Bob, thank you for an interesting perspective on the "independent sailer". I recognize myself to a large extent, but, not least because of the very lively discussions we've had on this forum, I'm beginning to be more open to changing long-held assumptions and preferences.
As far as DSA is concerned, there are three things. One, which I've commented on before, is the formal statement of the organizations purpose as set forth in the bylaws. That particualr formal statement is very focused on racing and seems to be out of synch to what you describe, which is the second thing, namely the actual range of activities that the people who make up the organization actually engage in. That appears to be considerably broader than covered by the bylaws - which implies that the latter should be updated to bring them into alignment with both the membership and the demographics of the class.
Finally, the third element is specific initiatives of the kind you described, and which are not "round-the-buoy" racing. One thing that I could find interesting would be a long distance "race". Perhaps not on as grand a scale as the Texas200, but nevertheless something where you go for perhaps a day-long course around a suitable island somewhere.
Have there been initiatives in that direction in the past?