Here's an update on my situation. I rubberbanded a diamond lap to the Sharpmaker with a rod stuck underneath the base. I forgot if it was wedged in the middle or the end, but I was thinking it should have been around 10 degrees. For kicks I used some marker, and to my amazement the right side was didn't match the left. I was getting scratch marks before that I thought extended to the edge, but the marker revealed that it really didn't, and the bevels weres at different angles before to approximately the same height. Anyways, I worked on them so they had the same angle (except an area near the tip on the obtuse side) and then sharpen them at 20 degrees, still getting some burring issues, but not as bad as before.
I give the VG10 Caly Jr and a sharpened S30V Military to a friend to try them out for a while. I thought the Military was fairly sharp, ahead of the Caly Jr. But in any case their grinds and edges should be highly functional regardless. After some days I ask for a assessment, and they (my friend and their architect brother) remarked it wasn't as sharp as their 530 Benchmade in 440C, which they had for a year and I exclusively sharpened for them using 15 per side factory bevel and 20 micro.
I thought the S30V should have been comparable. But it may have something to do with nostaliga as due to certain circumstances they no longer had possession of the 530 as of the beginning of the summer. In any case the 440C was a pleasure to sharpen. It didn't feel like Aus8/440A (non-Benchmade) being more more wear resistant, but it was very crisp.
But on the other hand, they are outside the knife world and hence outside much of the hype, biases, and other subjective influences, so their assessment is in some ways more pure.