Goldilocks and the Three Boats

[Riggerdood]

Not sure how the boats in dry storage actually get down to the water.

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Straander, my guess would be those two yellow cranes at the lower right in the pic. At the Santa Cruz Harbor, the only mast up dry storage is at the yacht club, and they crane launch them.

[CapnK]

<snip>...I've been pursuing an answer to the question of what boat is minimally viable for extended sea travel, and more than one captain has said to me, "If the boat can be "trailer-sailed" it's not really sea-worthy in all conditions I'm bound to face.  FWIW.

Hmm. Info is usually only as good as the source. Ask that same question of:
Robert Manry on Tinkerbelle.
Or Webb Chiles, on one of several boats - from an 18' open Drascombe Lugger, and up - for IIRC 5 circumnavigations now.
Or 'Ant' Steward.
John Guzzwell.
Roger Taylor, and/or most of the participants of the Jester Challenge...
Or... well, its a list that goes on much longer. You'll get a different sort of answer. 

Not to say that just any trailer sailor can go dunk the boat and return home some months later, coming from the opposite cardinal point. BUT - a small boat well found, with a prepared skipper, have made many a surprising voyage over the years.

[MeWoods]

There are two ramps to the north of dry storage location. (re: Dry Moorage at Shilshole)

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Used boats of decent size can be had fairly inexpensively. If you can and are wiling to do the work yourself it may be viable. I have a P21 but want to cruise the Maine coast. I may go more performance oriented like a J boat. I took a quick look at those storage option and yeah pretty pricey. However, there is no substitute for the convince of jumping on and going. If you sail often maybe a year in a slip is an expense you can swing for a really awesome year of sailing. I'd put your name on waiting list for either or both while you decide. I'm fortunate to have a mooring ball in my harbor. I'm on the waiting list for my second. Very inexpensive option. Dinghy storage is free. I jump on our dinghy and I'm on my boat in 4 minutes ready to go.