Do all those question marks mean you're not sure if you have 5 children???? Because if you do, you've already missed the boat (if you will) on "enjoying life" and not wanting to be "tied down more with committments" (sic). So, do you want to learn to sail/race? Those question marks again . . . . In Annapolis, there ought to be plenty of opportunities to start as rail meat and go on from there, but no racer will take you seriously if you don't show up most weeks. If that kind of commitment is too much for you, then maybe that's your weakness, not the urge to sail.