Rig weight and Stepping Mandate
Seth picked the # we use as the estimated maximum weight for our O-34 rig, which is probably on the heavy end since we pull all the halyards and run messengers prior to pulling up 'neath the crane @ ColYC. Except for being a bit unweildy, the procedure is not that big of of a deal, now that' we've done it a few times. 27 minutes from tie-up to push-off last fall to un-step (personal best!). Stepping takes a bit longer, historically, as aiming the mast through the hole in the cabin top and seating it on the base plate requires more TLC than yanking it out the top.
As to the premise of
'You Gotta Unstep blah, blah blah...', I submit these Google Earth views of Crowley's Yacht Yard and Hammond Marina, both located on the south side of Chicago. Crowley's is not more than 1 mile (using either mile measurement!) from Lake Michigan. Yes, it can get a bit windy, from every compass point. (knock on wood) Thus far, no domino effects at this yard, but these boats are predominantly stored on cradles and not supported via jack-stands.
Further south, approximately 4+ miles SSE, at the Hammond Marina in Indiana, 100% of thos boats are stored outside, mast up, on jack stands. And this location is less than 100
feet from Lake Michigan. Also no domino effect; also windy. A crew comes from Marblehead MA each spring and fall, hauling a big trailer, and picks, pulls and floats all the boats in 1 day before the head off to their next marina to do the same.
Everyone approaches things differently , from a different point of view. This mast up POV is common in this neck of the woods.