I am also new to ownership in the past year and am loving the wealth of information on the site.
Ciao #282 was in very good condition but there is always more work to be done. I have a friend down in St. Croix and I just visit last year. He recently bout a Stiletto 27. Never know we can maybe meet up.
I ended up buying a part off a girl that had a totaled j30 in the BVI from the 2017 storms. I really don't think she has the hull and bulk of boat anymore but I can shoot her a message.
Corpus Christi is very windy USVI also has lots of wind. I ended up going with a furler and a new #3 headsail.
I am more familiar with my local PHRF and no nothing of CSA. The J/30 as designed in OD configuration takes a hit in my region and most others for having the #1 163% genoa in sail inventory(a 155% gives me no penalty and lucky enough one came with the boat). Also the OD spinnaker pole that is J+1 in length gives a handicap hit. The addition of the furler gives me a better handicap.
If CSA works like PHRF, I would just say to be sure of the sail and spinnaker pole limits within the CSA and reduce your rating if the OD configuration is making you take a hit.