Good to get some ideas out there. I think Kaleb's has a lot of merit, as the person who contributes most to the monthly scores for the team (ie those that make up the final points for the month) is probably most deserving of getting a trophy for their efforts and is likely to have committed a lot more time and effort to the competition than the person who may only target a few epic sessions and takes out the top spot.
I reckon each time we get a trophy (assuming one day we may be lucky enough to win another) we should make them into perpetual ones, so we can have a bit of a list going

Be good to hear others thoughts on how the following should perhaps be ranked:
Top of the GPS TC ladder - Perpetual Trophy (already in place)
Most contributions to monthly GPS TC for the year
Most improved GPS sailor (probably voted on by other team members, or calculated some way via PB's)
Second Place on the GPS TC ladder
PS We'll need to decide by 31st December 2010!!