It's too much for Nylander, who may not succeed under Hynes. Kerfoot and Kase are less than ideal replacements for Jeannot and Trenin. NSH declines.

So on Opening Day 2023 we have nothing to show for trading 5 years of John Gibson.
Assuming for the sake of argument that the over-the-horizon second and two firsts are payment for Gibson (even though they won't show up until 2026 at the earliest), Vaakanainen is a better prospect than Hirvonen and the third is an overpay for Holl, so where's the compensation for the $7 million in retention plus the fourth?

You're right 100%. Honestly I think it would make more sense for them to re-sign Campbell or Kuemper for around $5-$6million if possible. Would Holl for a fourth be reasonable?

How about the new proposed deal - is that better?

Yes and yes. As to your first point, Dubas made a great trade by which he divested the team of Mrazek's cap hit without having to buy him out or retain on him, so it makes sense to try to go after one of the remaining free agent starters. And I think that's exactly why Dubas made that trade.

As to your question, a fourth for Holl is entirely reasonable, and I wouldn't be surprised if someone pays a third for him, but I don't think that the team acquiring him will be a non-contender because he has only one year left on his contract -- it doesn't do a rebuilding team to have one year of a rental middle defenseman. And us Ducks fans accept the reality that we won't be sniffing the playoffs this season.

In a vacuum, the value isn't bad. The main issues though are that NSH isn't going to entertain including Jeannot in any trade, and despite his considerable skill, Nylander likely isn't a great fit for the Preds. NSH is also taking on a lot of salary here, without sending barely any back.

I see that you're new around CF (and welcome!), but Leafs fans have tried hundreds of variations of Nylander for Jeannot deals since their season ended. None of them make sense for NSH.