I leave all my stays and shrouds attached to the mast and boat but have them
covered with snap on cable covers so as not to mark or scratch the boat. I
also tie a small line around each side of the cockpit rails and shrouds to
keep them secure.
I just started to keep my jenny sail furled to my self furling rig and hang it
under the mast with a number of small ropes. Also I am rolling my mainsail,
with the
first and second reef attached, around the boom and store it in the cabin. I
find this to save me a lot of time setting up the boat.
I have the same outboard as you and right now I store it in my car trunk. I
don't think it is a good idea to leave it on the boat. With all the jarring, I
think it will be hard on your motor mount where it is attached to your
transom.
I believe that most of the wear and tear on our boats will occur while
trailering.
Wes Harrison
P-19 FriendShip
Sunnyvale CA