Aloha and welcome aboard!
Thank you for your service
. In a few months it'll be 20 years since I retired from the Navy
. Time flies when you are busier than a one armed paper hanger.
Just as a suggestion I would put your number 2 item in front of your number 1 item by taking a basic sailing class to see if it is to your liking.
Many coastal military installations (and some inland) offer sailing lessons
. Some even rent small boats for you to practice your newly acquired skills. I learned at an Army MWR in Cheimsee, Germany
many years ago. Any military installation
will honor your newly acquired retired military ID Card.
It is truly good to have you here.