Re: My Rough plan to get better at sailing.
This sounds like a great plan. The $184 per month seems a little steep but maybe that's the going rate in your area; besides, it does allow you an array of boats for overnight trips and in multiple locations, so there is a lot of value there. In my case, I started sailing 4 years ago (as a totally green crew - knew nothing) and then began a serious quest for my own boat 3 years ago. I read and reviewed practically every boat under the sun, took everyone's advice, asked endless questions, sailed as much as I could, and then pulled the trigger a few months ago. There are still so many things I don't understand about how different boats sail under different conditions, but overall, I know why I made the decisions I did and the boat feels right for me. The best bit of advice was from someone who said, "what is the thing you can't live without?" This helped me focus. Depending on what you're looking for, you'll always have to make some compromises, but knowing why you made these choices is key. I suggest that, as you're sailing these different boats, you make a list of all the things you like and don't like as well as general layout, # of heads, location of berths, galley set up, storage, bilge location, engine accessibility, engine type and hp, sail handling, ease of reefing and raising the sails, location of sheets and halyards, etc. Have FUN!!