J - this seems like a very well thought out and well written post - are you sure it's really you?!
It's going to be very difficult to make everyone pay. and nigh on impossible to raise £500 - if indeed that was what was needed. But you never know - there are plenty of other ways we could raise money a bit, and I am happy to help out as always - the only other issue is some more funds may also be needed for some other ideas people may or may not have, so that could be a factor too.
I have made no secret of my vote for "background music only" - my only reasoning for this is basically down to space, and weather. In 2008 I'm sure we can all remember freezing our asses off sat outside because it was too loud inside to talk. So I would guess that if we were to go down the "music" route we would need a happy balance of quiet and loud times, or a lot of luck with the weather/temperature. The other thing to consider - if we are talking £500 - is - is that the best use of £500?
You make a very good point about the "global audience" too. Last year we went up to nearly 40 cars and 100 people, and I think certainly this year could well beat that (if I can get them all in!).
Also - does anyone (at all!) have any comments on what the point of Saturday afternoon/early evening is about? I know that this year only half the cars actually ventured out - is that because the rest were broken? Or are people happy staying in?