Thanks for the replies to date - especially the rough estimate for time, which I understand is rough based on so many things.
My handle - yes, I thought that it might seem odd to those that know the tale! But its frequently been mine on message boards - it was my favorite story in the Silmarilion. I guess even if it ended badly, there was a long age of glory, and well, I wouldn't mind having that before the end! But I'd kind of like to avoid entanglements with Sauron....
I live in New York City, so there are a lot of possibilities in the tri-state area for sailing. To meet our schedule, in fact, our courses are planned over three schools, one in CT, one in NY, and one in NJ.
I had done a lot of reading and based on theory, thought for what we'd like (long term), a multihull like a cat seemed right. Proponents argue that well designed and not-overloaded cats can perform very well as cruising vessels. But there is not a single cat in the area that is available for chartering or part of a club (there is one for crewed chartering and the ASA-114 course, but not for anything else). So most of our practice would be on monohulls. At least I'll get to know both types of boat this way.
Thanks also for the list of topics we would have to know AND be comfortable with. And the idea of having personal experience over classroom is appreciated. I had hoped to do any initial bareboat chartering is a limited sailing region - the Northern Sporades islands are close to my wife's home in Greece and are all within site of each other for the most part. We've also considered BVI etc., but that would be for another season, but may indeed be where we decide to do this. Chartering a skipper may also be in the plan.
I'll try to read up more on the forum as suggested. I'm sure more questions would be answered there. Again thanks for your responses and any more that come!
ps So any thoughts on why sailing is so expensive? Is it that its just not practiced in large numbers (so no economy of scale benefits)? The technology is expensive? It's a "luxury" pursuit? I was prepared for courses to cost a bit, but not so much for everything else to cost so much as well!
But it is a dream. My wife definitely has the Greek blood for the sea. I honestly think she gains in health and happiness just being near it for a while!