Maybe try a slight rounding off of the plane blades' edge? Just noticing some dig-in, but that could be from that "wild-grained stock". Pine? Is the Workmate holding up well to your plane stroke, or no? Tom
Rounding off is a good Idea. Bench stability also. My observations:
Blade depth is too great, shavings seem too thick. Blade edge not square to sole, protruding out more on one side. With a less aggressive cut you will be able to feather in and feather out with the plane without leaving blade marks. Some of the pics show some ragged grain after the cut. Check your direction of cut. plane "downhill and make sure the cutter is SHARP it seems not be be based on the pix. You should be able to shave the hair on your arm with ease when sharp. U won't be able to plane the full length of the board with the workmate cut it into short sectionsthat rest entirely of the bench to practice Work with stock wider that the plane to keep the body entirely on the stock
After looking at more pics it looks like you are really close to getting it right
Scot