Steve,

The only active cat sailing group in on Oahu. See http://www.catsailor.com/forums/ubbthreads.php?ubb=postlist&Board=14&page=1 for their infrequent posts. The rest of us are lone wolves. I don't recall any posts from anyone on Kauai. It's a shame as there are plenty of beaches all over the islands.

Good luck on your new life in the islands. Kauai is pretty quiet and should be a great place to decompress. If you need a big city fix you can hop on Island Air and be in Honolulu in a half hour.

Hawaii politics? It would take a long time to discuss all the nuances at the state level and each island has their own deal going.