Hey John, great write-up! All good lessons learned, and a positive outcome out of a scary experience. I haven’t hiked seriously in years, but I did a bunch of hiking and mountain climbing in my early 20s. I would say that your biggest issue here was jumping straight into a multi-day live-out-of-your-pack adventure. Step 1 is a single day trip (try 9am to 5pm), and step 2 is just adding an overnight component. I would rinse and repeat that a few times — you’ll start to pick up your own tips that way, and test your comfort level. Do you prefer going for miles, or the destination, or the scenery along the way? Do you prefer heavy packing or light packing? Do you prefer a certain season? Which foods work best for you? And you’ll naturally make small mistakes along the way, for example with your shoe choice, without having to live with it for too long.
Again the lessons you learned here are invaluable, but a lot of them are more applicable to 3–7 day hikes as opposed to 1 day or 2 days/1 night hikes. I guess I would say the 3rd day is the turning point where you have to start getting way more serious — and that can sort of take the fun out of it, and it becomes a logistical experience (because survival is important, of course).