Sean, you may have a damaged or badly worn flywheel. If you are in position to remove the starter, shine a light into the opening and take a look for a damaged gear
. If nothing is visible, feel the gear
with your finger (carefully, if it is burred it will be sharp). If there is a burred edge, that is likely the problem.
As for my comment about seamanship, I stand by it. Good seamanship includes allowing plenty of searoom, keeping the rig in top shape, having a contingincy plan for any failure of the rig or sails
, and having an anchor
ready to deploy when not in open water
. Granted, a set of sweeps is not a practical back-up system on a 40 footer, but on a smaller boat it is very effective. When the wind
fails, having an engine
to get you in is a matter of convenience. Otherwise, you wait. IMHO that is just part of sailing.