If I'm not mistaken since the seedings were a couple of years ...
We don't know what could've happened. I remember quite a bit of people at IHN during that time were sure the Canucks weren't going to get past the next round after they beat the Hawks. Let alone get to Game 7 of the Final. Being able to keep Ladd would've been a huge help during the playoffs, especially with Bolland being injured through the first few games of that series. That would've been a differently played series at the very least.
You can keep saying that amount of difference in cap space is negligible, but a million or so dollars worth of cap space this off season and the Hawks keep Leddy and all of a sudden the d pairings look quite a bit better instead of having that carousal of shit of the third pair. I don't buy that he was being moved regardless this season, it was only because someone
had to be moved because they were over the cap and no one wanted to take Versteeg. With his cap hit and his age and potential (and no fucking NTC that Stan was giving out like they were going out of style) he was by far the easiest to move out of the potential players that could've been.
In regards to the contract for Crawford, I answered that question, as I have before, from the aspect of what I would give him. Around 4 million is my cut off for goalie contracts with a team like the Hawks. Because you can still move a contract like that if you need the cap space or things aren't working out. After that, once you start getting into or 6 or 7 million dollar contracts, and especially the longer the contract goes for, it's not a contract that can easily be moved.
As far as the roster for next season goes with your scenario of losing both Bickell and Crawford with no cap hit in return (which would be awesome and also a miracle) tack on a million more to Kruger and you probably keep him a few more years. He's an RFA,as are most of those players you listed as having to be replaced. The hardest spot to replace would be Oduya's, because teams seem to go bat shit crazy over mediocre d-men in free agency.
But you're gonna have to eventually play guys who have "no proof" at this level at some point and I'd rather keep experienced forward depth (or blue line depth if the scenario is Seabrook being moved instead, which would be even worse), especially players that are strong in puck possession in that to help those players with "no proof" along than to lose that AND rely more on your goalie at the same time AND expect more from those types of players and rookies right off the bat because of it.
And that's probably where this going to end again because you don't think a team has that big an effect on their goalie.