To address you once again, YES! when you are talking about an elite talent, a top 10, possibly top 5 player in the league, Yes, of COURSE teams will go through all of that to get him. Don't see why you don't think that is possible. You want a guy that is a MVP level player, teams will do that.
Not to mention that he may be more valuable to other teams than the Leafs. His talent will be the same for anyone else on the ice but the Leafs don't need the extra draw/attention his marketing brings. To other teams the attention and revenue he brings will likely be more important to them.
And as far as Cap room, pieces will be coming back to the Leafs. If a team is right up to the cap or over it...there may be an issue, but they don't need to have $12.4m in cap space. They will likely be sending some cap space back, and to fit a talent like AM, they can make other moves to clear space.
Again, when you are talking a talent like AM, other teams WILL do things beyond what they would for other players who are just 'good' or 'stars'.
It depends. If you get the 2021-22 version of him, he is worth that much. That isnt out of the question either as he should still be in his statistical prime for 3-4 more years.
Plus $14m over 2-3 years isn't as ideal as $14 over 6 or 7 years. If he gets 6 or 7, he is still in (or close to) his prime toward the end of that contract, but the end of the contract likely has a higher cap so those years are less of a percentage.
If you give him $14m, in a perfect world that is 4-5 years for me and I'd do that.