Thanks to everyone for their great comments... I'm slowly moving ahead with my plan, and adjusting it to "be careful and respectful of mother nature and the oceans around me".
I'v also looking at a 1971 Islander 23 which is in decent condition to start, and has a trailer so I can avoid mooring charges for a little while.
Hope to share a drink with some of you planners in the islands one day. Be good, be smart, be safe, and be well. Enjoy today in a way that you won't regret it tomorrow and we will have a much better chance to share that drink :-)