Ah! As I said before, you are learning
That's very good! Read and cogitate on Stu's post. As you will recognize, he and I are coming at the same "problem" in different ways. The really significant thing is that your present plan is perfectly realizable, which the one you came in with didn't seem to be.
I have taught people to sail on boats from 13 feet to 65 feet. To a degree, boat handling is the same whatever the size of boat. HOWEVER: In a small boat
muck-ups are generally not very serious and mostly good for a giggle. In a small boat
"stuff" happens quickly but is rarely serious or expensive to repair. In a big boat "stuff" happens very slowly as a series of cascading catastrophes, and it is almost always serious, and always expensive to fix. So starting on a little 'un is a sensible thing to do.
You could pick up a used Cal 20
, say, for fifteen hunnert bux and learn on it. Or you could zip out to Jericho and simply join the Locarno Sailing Club so you can use their boats (against a fee of course). If you are gonna live ashore anyway, I cannot recommend joining a suitable club too highly. Locarno is a direct descendant of the Simon Fraser University Sailing Club which I and some friends started in 1968. I lost
track of how many students I gave "the basics" on Enterprise dinghies. For the now defunct JibSet sailing club I taught a lot of people on the aforementioned Cal20. A little further up the scale, the JibSet used Catalina
27s to get people to the point where it was safe to let them loose on this 'ere coast. I came to LOATHE that boat, but that's a whole other story. You could get one of those for six or seven grand (if you can find a place to park it). It'll be bare, but that is good, for that'll give you chance to learn quickly, and to decide what YOU need (or want) in a small cruisier, and it's perfectly adequate for taking a man and his maid to any of the popular cruising destinations around here, such as Princess Louisa Inlet.
So now the time has come to tell you that boat handling I can teach you in a week end. That's the least of it. And you mustn't confuse the ability to take a Catalina
27 safely over to, say, Buccaneer Bay and back again on a summer weekend with being a skipper
But you could also go to Cooper's Yachts on Granville Island. They are really a proprietary Club as well as a brokerage and Lord knows what, and they teach you on good boats - for about the same amount of money
that would buy you a Catalina 27:-). And the annual dues are about the same as moorage for a 27 footer would cost you in my marina on the Island. Cooper's bought out the JibSet when Les Alfreds, the JibSet's proprietor, went to Fiddler's Green.