Re: asa school vs buying own 20-30ft and teach self?
As someone who took up sailing by enrolling in an 8-day ASA series (101, 103 & 104) in Santa Barbara (mostly on a Catalina 42), followed that with a summer timeshare on Lake Michigan (Jeanneau 42), then chartered for two weeks in the San Juan Islands, during one week of which my wife completed the 101, 103 & 104 sequence (Islander 32), I made my way into sailing via classes on larger boats. I learned a lot (especially about how much there is to learn), and loved every minute of it! Our plan was to do our sailing by chartering a couple of weeks each year.
Note the "was" in that last sentence. Chartering is great, but for us it just wasn't enough sailing. Last month we bought a used sailboat (Beneteau 210) and put it in a slip at the nearest sailing lake - about 1.5 hours away. We don't have the crazy tides and roaring currents of the PNW to contend with in planning routes (San Juan Islands), we don't have to watch for freighters on the way to the Channel Islands for a night's anchorage (Santa Barbara), nor do we have the city lights of Chicago to gaze upon during a warm summer evening (while keeping a sharp eye out for powerboaters). And it is a heck of a lot easier to dock a 21 foot boat than a 40 footer.
OK, the sailing challenges aren't the same, but there still are challenges: hanking on sails, rather than working a furler. Making sure that *your* boat is shipshape and safe. Balancing the boat with one's own body weight. Sheeting the jib without a winch. It's more elemental. I've discovered that my spouse is a better sailor than I, no doubt because her father bought her a (wood) X-boat and she sailed it alone on a Minnesota lake as a teenager. I'm learning a lot from her. I have found that I can sail this boat single-handed, and that too is a benefit.
So, all this is to say - coming from someone who did the classes and learned on bigger boats - buy your own boat and head for the lake. Something you can sail with one or two crew as well as sail alone. Something you can trailer and set up in 30 minutes max, ideally by yourself. A daysailer would do that for you, and there are a lot of O'Day 17s around on Craigslist for $2500 or so (some have mast steps that make them easy to rig). Go much bigger or heavier, and you will need either a tow vehicle or a slip, and neither is inexpensive. Plus, boats at the upper end of the 20-30 foot range often come with expensive and unreliable systems like marine heads, pressure water systems, stoves, and the like.
As I said, the classes are great - and if you can join a local sailing club so much the better. But find a way to get out on the water with the boat (hopefully) under your control in a freshening breeze.