I have read all the advice given to the OP, good and bad and drifting, and now I'd like to suggest a workable game
plan for him.
Veto, you live in an area not known for yachting activity, especially "blue water" activity. You could spend a bit of time and a lot of money
travelling to areas where formal lessons in keel
boats are available. But while lessons are good for some folks's learning
curves, I think we all agree that hands on experience in your own boat is where the most learning
goes on, and the above plan doesn't provide that very well.
Here's what I would do in your place (and you may have already started on this route):
First, avail yourself of all the non-participatory learning that you can... reading in the vast literature of the sea and sailing, including both how to do it books
and tales of others adventures. Videos and other media material abounds on the net, and can be helpful too.
Second, start looking for a sailing dinghy
of your own. IMO, this should be in the order of 12-16 feet long, sloop
rigged, on a trailer, and in good enough shape to just be sailed as is. Even in Colorado, I bet there are numerous examples around, and the cost should not be awful... perhaps a grand or less. Then, armed with your book learning and your new dinghy
, when the lakes melt in the spring, off you go to start the experience gathering process. Start on a mild day, rig only the mainsail and go sailing. Wear a PFD
and don't worry about capsize
or other happenings. I bet that within a few hours you will be tacking and gybing with some feel for how it should go. Then you add the jib
and start over. Repeat every chance you get all summer long...
You will have a good time, you will learn by doing and eventually you will outgrow the lakes and the dinghy. That's the time to be considering what sort of bigger boat will meet your (probably changed) plans. Selling the dinghy for close to your cost should be possible, and then you may come back to us with some greater idea of reality and seek our advice about boat choices (if you feel the need).
The next stage will involve not so much learning to sail your bigger boat, but how to deal with all its complexities. Having achieved your basic sailing skills means that you can concentrate on the learning of the boat without the anxieties of a neophyte sailor. IMO, this is a big deal... others will likely disagree, but I've watched a lot of newbies with complicated boats get so swamped with the combination of beginning sailing and new boat issues that their dream faded and never materialized.
All this while, you should be studying things like piloting/navigation, rules of the road, engine
and electrical maintenance
and all the other skills needed by a solo sailor, for whom self sufficiency is mandatory. This sort of study is a good winter plan (I hate winter) and will keep your eyes on the tropical future.
BTW, the reason I'm pretty sure this sort of plan can work is... it worked for me! Only difference is that I bought that first dinghy the very next weekend after I went for my very first sail, and didn't have anything like the resources available to you. I lived in California
so the wx was a bit kinder, and the local library had a good selection of sailing books.
Finally, don't let the guff about the dangers of single handing scare you off. Yes, it is more hazardous than with a skilled crew, but no, it isn't foolhardy. The success stories of countless singlehanders, all ages, all sorts of backgrounds, seems to prove that it can be done.
Good luck and let us know how you get on.