Looked up those places online, and that is some extensive Ribbing and trailering! Nice work. I too had my first season in a Ribcraft 5.85 last season. Did about the same in total nm travelled (1235), but mostly because I commuted to work 28 times (28 x 18 x 2 = 1008nm).
Never got too far from home, furthest was off Provincetown at about 42nm each way.
We don't have on-the-water courses like you guys have other there. I did take Seamanship and Navigation through the CG Aux, but it was largely review as I am what I think you would term a 'yottie'.
Worst weather by far was the Rib Rendez-Vous. I guess it was only a F5 or F6. All I know is that all sailboat racing was cancelled, and that the entire RIB was out of the water numerous times.
Hope to do some more distance trips this year. Also, picked up some lobster pots, and will work on the best way to pull those aboard.