John, I strongly believe your approach to learning by doing is not the way to go. You need some instruction to keep from wasting wood, or worse, hurting yourself. I took woodworking in junior high and learned enough to keep all my fingers. Most of what I have learned has been from reading ww magazines or watching the numerous PBS shows. Norm Abrams taught me more than any other source. Still, I have burned more wood than I care to calculate as a result of teaching myself through trial and error.
I would not take advise you use the rough local oak for your projects. It's not really very user friendly, especially without power tools. Trying to take out the bows, twists, and cups from sawmill lumber isn't going to be very rewarding. Buy what you need at Lowe's or the like. Buy the cheapest grade of pine and make the same project over and over. Choose something useful so you can give them away. Doing the same thing over and over will help you learn from your mistakes.
You can no doubt find DVD's of Norm's, Scott Phillips's, or Tommy McDonald's lessons. Start with a simple project like a step stool. When you buy tools, buy the very best you can afford. Cheap tools aren't going to help you learn. Since you are unfamiliar with hand tools, I wouldn't buy at a flea market.
The best thing you could do is find a woodworking school that gives weekend classes. A couple of nights in a hotel and some meals is going to be worth some hands on instruction by someone who already made the mistakes. It is very frustrating to ruin a piece of wood because you didn't know how to cut, plane, or join it.
Get help, John! Doing things like using a 2x4 for a fence is just asking for an accident.
