Dave,

I belong in the treasure the old tools camp. Many of my tools were handed down to me, and many (most) were not top of the line tools in their day. With that being said, however, I know from first hand experience that it can be frustrating to learn it all at once - fettling, sharpening, reading grain, technique, and troubleshooting what part you are doing wrong. I think that the advice given here as to selection of a new LN or Veritas is great. It will give you a benchmark for what a good plane should be. Also, the advise to learn to sharpen cannot be over emphasized. You also have a great idea in the classes or club participation. A couple of things I would suggest also are: (1) Practice - A LOT. Take scraps, put them in the vise, and go to it. That more than anything will teach you the feeling, the technique, and even the sound a properly fettled plane makes. It will dull your irons, which will in turn lead to more practice - sharpening. And (2) once you get a feel for it, and think you know exactly how a premium plane should behave, buy an old Stanley for $10 - $15, and make it behave that way. In the process, if you are like me, you will learn so much about how the design of these tools, new and old, can be persuaded to provide such satisfying results. To me, using a tool that I bought in a junked up state, then tuned and fettled it into a functional user just adds to the great feeling I get when I finish a project.

BTW - Be careful, Its called the slippery slope for a reason.

James