A great collection of advice. With the restrictions here, I decided that a small dinghy is the ticket, I have bought a Mutt 15'r and sailed her by myself last Sunday. Boy was it fun. I considered it a success for several reasons
1. I went sailing . Only got dunked once.
2. I went sailing. Found where my limits are right now.
3. I went sailing, got some practice and learned first hand how to control the boat.
4. I went sailing. I was able to get a lot of good input on what I did wrong to get the boat to capsize and will be able to avoid them in the future,.. maybe :-/
5. I went sailing.... and plan to go back
I don't think it would be a good to try to trailer-sail a larger boat at bluewater. The approach (ramp) is rather shallow, so I would have to put my truck completely under water to put in a keel boat
so I feel i made the right decision. As many have said... I'll learn better on a small boat, and will have a much more keen "feel" for sailing a bigger one. I plan, once I am doing a decent job, of buying a bigger boat (22-26) and keep her docked either at Heron or Elephant Butte. I should have completely retired so I can spend as much time as I want sailing.