Oh crap I forgot they traded back. I would say I think at the time (and now) picking either Caufield or Boldy would have been fine at 11. Arguments for either one being better now or long term for sure, but both would have been good picks at 11.
I honestly don't remember my thoughts on Harley or York from 2019 because I was not expecting either of them to the pick. My response was probably more being bummed about not getting Caufield or someone else like Newhook or Krebs.
2019 was the only real year I watched prospects significantly, and I had a 12,000 word write up that I did on the top ~30 players of the draft. I remember it fairly well because of it. I watch them now, but no where like that year -- mostly I just follow the Flyers draft picks.
I'm looking at my write up now, I had Harley 17 and York 19, basically in the same group of skaters. Harley had a great skillset. I wasn't fully sold on him as a player, but it was clear he had more skill and high end potential than York.
At the time, I would have been very upset with Harley at 11 or 14, and was very upset with York. However, In 2019, I was more comfortable taking a higher-floor/lower ceiling player vs the lower-floor/higher-ceiling type player. Now, I've recognized that getting a high-end skill player who can be a top-of-the-lineup type player is difficult, so I'm more inclined to take a swing on a player you believe in.