#1: Keith seems to have aged--especially mentally. His shooting/passing releases take for ever and his double-clutch hasn't been fooling anyone for years now. Further, on the back end he tries to do WAY too much--especially for other who blow their coverage. Anymore when he tries to cover for someone else he also loses his check and thus giving the goalie 2 uncovered players to deal with as opposed to 1. He may still be okay in footspeed but in terms of game execution he's not there anymore. That's not to say he's at the same level as, say, Rosival in terms of aging, but he's not the player he once was. It seemed to me when Joker was playing with him Joker had just enough raw talent/raw hockey IQ to take care of himself which helped Keith's game a bit. Overall though his game has regressed. His game in my opinion right now is that of a 3/4 guy on his own. With a competent partner he can probably be a 1/2. You just can't expect him to do anything on the PP and you definitely can't expect him to carry anyone anymore. That's not to say in the open market he couldn't fetch something that's valuable but if the NMC & Recaptures were not a thing his value would be maximized by trading him to a team that has a 1/2 or a 3/4 D-man left on an island without a competent partner as well. What Keith cannot be though is "The Guy" anymore. He once was but isn't anymore and I think other teams would see this--which limits his possible destinations further.
#2: In the Non-NMC and non-Recapture world, sure. That would be the target. We do live in that world, though.
#3: I would like to think we all want at least 1 amnesty buyout in the next CBA, but a few things have to happen: The Players union and/or the NHL have to opt out (likely but not guaranteed), the new CBA has to be drafted and agreed upon (hopefully without a strike/lockout), they have to agree to have amnesty buyouts (I'd like to think they will), and we'd have to hope that the CBA wouldn't have a clause precluding us from buying out the player we'd want to buy out. On it's face I don't think it would be an issue, but I also didn't think anyone saw Recapture being a thing.
Speaking of which when it comes to recapture, the TL;DR version is this: If Keith officially retires, the 'hawks have to pay up to 4M in a cap penalty--this is irrespective of whether or not we trade him--the 'hawks are on the hook. Thus, if Stan/McDonut pull some Pullford/$Bill crap on him, he can fire one hell of a parting shot. Thankfully, he's the last one of those we have.
You'd think they would but nothing is guaranteed. The flipside as well we have to watch out for is what clauses in the new CBA can hijack teams. As I alluded to above: I don't think may saw Recapture coming as a way to punish retirement contracts--like Keith & Hossa have. For all we know in the next CBA Prongering (going on permanent LTIR) is no longer viable. Let's say at that point there's 2 years left on Keith's deal and he's all used up. What then? Or, if what
@piteus is referring to happens, We trade Keith out and the same happens, but Progering is not allowed and the effects of recapture still affect the 'hawks. Again: hypothetical.
My point is that Keith's deal is a potential minefield at this point. Seabrook, Kan, Toews, etc. are straightforward--at least for now.