Interesting discussion and points here guys, taking it all in Nth of the Border also, we are still in final stages of plans on season 3..so wont comment on what the results of those are just yet, but its good to see this healthy chat here, shows interest and some passion is alive!
The 'same guys' always win thing does come up also....and yep, what can you do about that? Not much really cause that's life! There is always one guy in the Gym that benches 50% more than you, and there is always one Guy (sorry to be sexist) that wins the Club best and Fairest each year...that's how it goes..mostly they excel because they train/practice harder and are more talented....life is not fair or equal, it wasn't designed to be.
However!
We have recognised the 'levels' and 'standards' are not the same so to encourage all levels, we have the 3 grades, it's worked well.
Race, Freerace, Novice...
The Race Board/Sail/Slalom board guys go in Race.
Novice is Newbies/Intermediates and Newbies, works well..the Novices have the easier option of 1/2 hour,
Freerace is really aimed for those on freerace boards and sails, as they do have a slight average speed disadvantage over dedicated race gear...but are conversely much more fun to sail, so there is a few races within the race, but everyone is on the water together. Their is as many windsurfers that sail freerace or freeride gear as dedicated GPS/RACE this is who we are trying to attract with this class and Newbies as much as possible.
1 hr is not hard once you have done it a few times, your sailing stamina and skills improves greatly when you push the time out, then you start looking at 2 hr times!
Wind limits pretty well discard any advantage in bigger gear as we try not to go unless its 15Knts + average..so our average sail size is normally in the 7's and 6's.
The overall aim is to get as many people on the water of all different levels sailing at the same time in the one event, whilst keeping it ultra simple and easy to run and organise, we also only run when the Wind Gods say its windy..no point setting a firm date and hoping for wind on that exact day....rarely works...so in the past we aim for the first windy Sunday of the Month, easy...except when there is no wind on Sunday, but there is on Sat!

Overall we now have about an 80% +15knt success rate and out of that probably half of the events were in the 20+ range.
It's a constant work in progress and always looking at simple ways to improve...and probably the same as you guys , put together by a very small team of volunteers.