chris, in an effort to procrastinate from further fundraising activities, i read your entire proposal for your "dream doc".
i can safely say that you're CRAZY! having said that, i think it's a good kind of crazy, and the shared gene that most of us aspiring and established docmakers possess. plenty of people have been told their projects have absolutely no chance – and a fortunate few have actually persevered and finished their projects with great success.
however, i would really challenge you to re-evaluate WHY you are doing this project. at the same time, i would challenge you to think about why you are not doing a DIFFERENT documentary project. To me, this project seems too frivolous and insubstantial for someone like you, who admits to admiring the direct cinema and verite work of masters like Maysles, Kopple, James, etc... i'm no psychoanalyst, but you seem like you might have a more "worthy" doc in you to produce. by "worthy", i don't mean that it has to be intensely depressing or socially conscious – it can have humor and spontaneity and whatever else fits your personality – but it has to have something at its core that inspires you.
The "impossibility" of making something is not reason enough to try. You need to combine "impossible" with "irresistible" to really have a film worth making. if you write a proposal that convinces everyone why you "can't NOT make this film", then you actually might have a chance. right now, i read your proposal, and just see a guy who says "why not make this film"? there's a big difference.
i don't want to discourage you, just refocus you... btw, if i didn't think you had it in you to actually make a doc film, i wouldn't have wasted my time writing this reply. good luck!