I will probably try to get my hands on the "Annapolis Book of Seamanship" as from what you said it seems to cover more. There is a local college with a $500 course on sailing too that I will consider.
The closest body of water to me is lake Ontario (live in the Canadian Niagara region). A lot of the boat ramps I have seen are fairly gradual, so one thing on my mind was as one of you mentioned, is just how deep do you have to drive in with a fixed keel boat to get it deep enough. And of course if it was too steep pulling it out could be a problem.
The swing keeled ones are interesting but in my mind that is more maintenance/damage prone. I guess it might be a trade off I'd have to live with. I'd probably avoid bad weather anyways, but you never know.
I wouldn't mind going out with other people either for a day sail, maybe I'll check around with local clubs.