I agree whole heartedly to keep it a fun event and think it is an event to [plan for.

BUT I would spend $100+ in gas, $175+ in lodging, $100 in outside food/beer and $50 in registration (at least).

That's $400+. Should I expect fair racing or should I skip the event?

It is a hell of a lot easier to live there an push your boat off the beach (total investment of $50). I am a HUGE fan of this regatta, but it MAY get a reputation of not worth the effort.