Hiccup's unwillingness to tell his father that he has a bounty on his head was one of those things that's super frustrating while watching, yet it also made sense coming from Hiccup. Plus, what would the drama be if he'd actually told his dad?
It was cool getting to see Berk's 400 year anniversary. Actually, I wish we could have seen more of that celebration and possibly heard more of Berk's history. That would have been interesting. I love learning about the histories of other worlds in stories, which is most likely connected to my enjoyment of real world history. It would have been a cool addition to this episode, but I get why it didn't happen considering the nature of the show.
Something I find interesting is how many bounty hunters manage to get close to Hiccup when Viggo has been unsuccessful in getting to him himself. Viggo seems to be adequately full of himself for a villain, but apparently he suspected a lone bounty hunter or two would be able to capture Hiccup when Hiccup manages to evade Viggo's entire army on a regular basis. Of course, one bounty hunter was able to get Hiccup to the island, but I thought it was interesting that Viggo thought this plan might work considering how capable Hiccup has proven to be at getting out of such situations.
The bounty hunter who does manage to capture Hiccup is suitably mysterious, and it's presented in a way that makes me wonder if we'll ever see him again. We've seen him twice now, and he doesn't seem to be a two-shot villain either. Maybe I'm reading too much into things, but I swear we'll see him again, and I think it might be in the third movie. We know he's working for Drago, who was the villain of the second movie who is supposed to also be in the third movie. While Krogan wasn't in the second movie, I do have a slight suspicion that Krogan might be a character in the third movie. This isn't a theory I'm terribly tied to at the moment, but I wouldn't be surprised if that turns out to be the case. If so, I think it's pretty cool that they introduced him through Race to the Edge.