This isn't going to happen. Arizona is not going to help the Sharks out this season given their retention slot status. They will be saving that final slot for Kessel at the deadline or close to it. If this becomes an offseason issue to deal with when Kessel and Kuemper come off the books then a discussion may be had but that may not be given clearance to happen until after the buyout window which could complicate that option. There may be arbitration options to extend the buyout option but it's also possible the team just may not pursue it and buy Kane out when the window opens after the Finals. The Sharks certainly won't get out of having a third team retain for three seasons plus scot-free. The Coyotes won't retain 2.25 million for three plus seasons for a 2nd round pick. That's way undervaluing the service they're providing there. The value of a 3rd team retaining even just 1 mil for three seasons is going to be a 1st round pick. A price that the Sharks will not pay. A price that the team acquiring Kane will not pay either. The 3rd team option in this scenario is likely not feasible. The Sharks retaining half should mitigate the risk enough for an acquiring team should they believe that Kane the person/teammate is worth the risk. If you're willing to acquire Kane at 1.75 mil, you're willing to acquire him at 3.5 mil. Guys like Kane are either do-not-acquire or take him at half.
You're bang on with respect to what Arizona will do -- it's going to cost a lot more than a 2nd round pick to retain $2m for 3 years - regardless of team. Personally, I don't think a first even gets it done, unless it's a very good first.
That being said... to me the anaylsis of what San Jose should do breaks down as follows:
1. In a buyout scenario, Kane costs them an AVERAGE of $3.6m for the next 3 seasons, plus $1.6m for the 3 seasons after that.
2. A 50% retention trade costs them $3.5m for the next 3 seasons, and nothing after that. Therefore, they should be JUMPING at the possibility of trading him with 50% retained.
3. Obviously, there are no/limited biters today for Kane at $3.5m, and the consesus on HFboards seems to be that nobody wants the potential sideshow for the next 3 years at $3.5m.
4. Personally, I think there MIGHT be biters for Kane at $3.5m, but it's not a deal that can be done in-season, simply because of cap space constraints.
5. Based on that, I don't think the Sharks should really be in any rush to make a move. He's been good in the AHL, and teams will only view his AHL time as positive for his "rehabilitation". Let him play out the season there, and hope that, combined with teams having a bit more flexibility, that you can do a simple 50% retention deal and call it a day.
6. If that doesn't happen, then it becomes a question of "what is that $1.6m x 3 (starting in 3 years) worth to the sharks?" Is it worth a first round pick today? IMO, yes it should be... but that's a really tough sell from a PR standpoint.... trade Kane @50% plus a first to Arizona for nothing. Arizona retains say ~ $1.5m, and then trades Kane at $2m for a 2nd rounder?