Hey Andreh. As usual I would not want to make a guess about how your friend Henry might do in NTRP-based rated matchplay. I will say nice work on the videos. Nice quality and perspective. I always enjoy watching your vids. I'm working on getting mine up to the same quality. Will be getting a wide angle camera asap so that I can get the corners of the near court. Also am saving up for one of those fence mount things.
Anyway, my honest opinion from what I watched (all the "Henry" vids so far I think) is that you should be able to beat him. But if he beats you regularly as easy as you say, then it just goes to show that you can't tell much from a few minutes of video of casual hitting.
For example, I played a legit, solid 4.5 the other day. If you were to see snippets of me and him just hitting around before and after the match, you might guess my rating at a bit higher than 3.0 (hitting with good players tends to bring out the best in me and make me look better than I actually play) and I'm sure you'd guess his rating at a bit lower than 4.5. By the way, yes, he won 6-0 6-0. But it was fun for both of us I think. I think he made 1 or 2 unforced errors the entire match. If you were to see this guy practice rallying it's not readily apparent that his strokes are any better than yours or Henry's, or mine even (well, ok that's stretching it a bit, but you know what I mean
). What he does, with anticipation, quickness, movement, great court sense, etc. is that he continually puts himself into position to hit relatively easy shots. Which he almost never misses.
Anyway, thanks for the vids. Keep practicing, as I will.