We as fans might not have the full picture on this. It was suggested in the Friday interviews, by Shanahan I believe, that they've identified players who have not made the progress asked of them. These players, aren't becoming playoff performers, or doing what it takes to get there. Now from the tone, it really sounded like he was talking about young players growing their games, and be patient waiting for them to do so... Tavares wasn't a young player, and I don't think patience is part of the equation... so to me, Shanny was talking about one of Nylander, Matthews and Marner, not having what it takes to become what they need....
So the biggest problem, is removing the player(s), that lack the mentality to compete in the playoffs. Cap is kind of irrelevant, when you have key guys, who won't play to win, and are a detriment to the team. It's a bit of a addition by subtraction, even if they have great natural talent... now we've all speculated that's Marner.. and it probably is... so no matter what else is done... that player (Marner?) needs to be moved.
Moving JT might also be a problem, but less so if Marner(?)'s cap is removed. JT is also far less likely to waive, and plays a position that would be very difficult to replace him. The number of good replacement UFA 2C's is very small, while the next year is looking better for now. WIth JT's cap hit, it might actually cost us assets to move him... which isn't palatable at all.
So first, remove the players who are barriers to success... then deal with things from there.
Why do we need another LD, who is good on the PP, but needs sheltering defensively? I mean, if the plan is to move Rielly... ok... I mean I guess.. .but otherwise how does this make any sense? Especially if we continue to run basically one PP unit... maybe that changes under a new coach, who knows.