Great post TexasShaver, it actually got me to stop lurking! I am 3 months into SR shaving so many of the issues you wrote about are very familiar. Some things that helped me:
1: Paddle strop. I started with a 2 inch hanging strop and hacked it right up. Turns out stropping is not as easy as it looks. The paddle really helped me concentrate on good form and have confidence that I didn't just dull my razor.
2: Try a Hart. I have a variety of grinds but what really helped me not question the sharpness of my SR was a sharp edge that seems to maintains its sharpness longer than my others. Every SR I have behaves differently and as I learn it is nice to rotate back to a SR I know is sharp and delivers very smooth shaves every time. What more could a beginner ask for?
3: Depending on how your whiskers grow, every part of your face may require a different strategy after the first pass. I have facial hair that grows in different directions in different places. In order for me to get an exceptionally smooth shave I have to find the right combo of skin stretching, grips, and angles for each area.