I do not like many of his draft decisions because I think he and his group are convinced that they are simply smarter than everybody else when it comes to evaluating draft prospects. He even said this above:
..."And then probably the second part is when you've maybe identified a player that you think the industry at large will either undervalue or view differently than we do organizationally because of their relative strengths and relative weaknesses and then having the ability to acquire that player because you think that individual's strengths align with something that you value offensively or defensively where they can carve out a role and play well."
The Browns present draft room seems to approach the draft with an arrogant attitude that they are better than every other NFL draft room, yet their record says something different.
While the Browns draft room, under the leadership of Podesta, Haslam and Berry pretend to be smarter than the other 31 NFL draft teams, the Browns record "for selecting superior draft talent" indicates that this Browns draft team is nothing more than average.
Reviewing the Browns draft record speaks for itself... link
...hmmmmmmm... people on this board complaining about someone else's arrogance? If by arrogant you mean not worried about what outsiders think, then sure. Otherwise, I think that Berry's operation is pretty humble as he takes a lot of input from everywhere. If you want to talk about an arrogant GM, look at John Dorsey. Dorsey didn't want input from anybody.
If Watson plays well and we win a Super Bowl next year, the value provided by those 1st round picks goes way up. Unfortunately, the draft isn't disconnected from the rest of roster building. When you trade picks for players, you are going to get less out of the draft (specifically) than you would have otherwise. Yet, you can still end up with a better overall team that way. It sucks that Watson has missed a lot of time. You can't really know about injuries in advance, though.
Do I love the Watson trade so far? No. But, if Watson lives up to his potential it can still work out. We weren't going to be picking top 10 to get a different good QB without giving up similar draft capital to what we gave up for DW. Baker had worn out his welcome.
We have a good team. You seem to be overly myopic on the draft. I get that it is draft season. Still, draft capital can provide value at other times as well.
A GM's job isn't just to draft good players. It's to add as much value to the team through whatever avenue he can do so most efficiently. Berry's been able to "steal" some good players like Amari Cooper and Za'Darius Smith (Hopefully Jeudy) for late round draft picks. (I think those guys tie in to the industry undervaluing players idea that you quoted.) Are those figured into your "draft record?"
To me, it ultimately comes down to "Is the team better now than it was when Berry took over?" Personally, that's an easy yes. It's one of the best rosters in the league.