Re: Does a first sail ever go as planned?
Nicely written tale; I enjoyed it, thanks.
A packing gland should leak a little bit, maybe a couple of drips a minute in the slip and a bit more under way. The water lubricates the packing. It needs to be tightened periodically, so check it every now and then. The flax packing can actually cut a stainless shaft, so do not tighten it too much.
As to plans, back up plans and plans for when all those fail, relax. You can't plan for every contingency so don't get overly caught up in that whole thing. Murphy (you know, of Murphy's Law) had a couple of boats and that's where he got the idea for his law from.
Sailing, whether on a lake like you do, or inter island as we do, is supposed to be fun, so don't stress out about the improbable, probable or even possible; whatever comes, you will manage to get through just fine, though most likely, not according to plan.
"Any idiot can make a boat go; it takes a sailor to stop one." Spike Africa aboard the schooner Wanderer in Sausalito, Ca. 1964.