why not wager based on turnout like this:

For each boat registered, Division earns 1 point (equal to 1/5 of designated liquor).

Division with most # of points wins.

Losing division sends winning division amount of liquor equal to NET LOSS (winning total - losing total = net loss) to be equally distributed at winning division's next function

what say ye?

(Even pirates can be democratic...arrrg)