Hi Dan - I'm going to give you the perspective of someone who has just left the "discouraged stage." I tried free hand and jigs on different media all the while feeling discouraged. I found that trying to sharpen in a vacuum and not as part of some woodworking project didn't work for me. I became fixed on some abstract ideal of sharpness rather than sharp enough to use the tool for the job at hand. I found that using a simple method that didn't stress me out meant I would sharpen/touch up often which lead to better results. And I got better with the frequent, short sharpening sessions. Here's what I do with no claim other than it helped me. I try to sharpen everything free-hand to 30 degrees. After using an angle indicator to practice at 30 degrees, it's become almost my automatic. I don't put a micro-bevel because the full bevel helps me register the correct angle I'm honing. I use a soft washita, then a black hard Ark, and then I use a buffer. Check out David Weaver's youtube channel for the buffer. It's actually simple, quick and I've yet to get a blade as sharpe freehand with a strop as I do with the buffer. Unless the blade is chipped or I've put the bevel out of whack, I can get a blade back working well w/ maybe 15 strokes per stone and two full passes on the buffer. So all together less than 3 minutes. Another thing I learned that I don't see people mention much is the importance paying attention to feeling the blade contacting the stone. Now I found I can feel right away when I've got the right angle and stroke and when I'm messing up. I also found I had to learn to feel the correct burr. In the beginning I tried to get a large burr, almost like a moraine. Now I swipe until I feel a very small burr that's even across the back of the edge.

This is just my journey, and even if you find something else more helpful, I want you to know that you'll get past being discouraged and then wonder why you worried so much.

Eric