I admire your consistency in perspective but I think it's still a tad optimistic.
I think anything but a long term deal out of the gate signals a shortened tenure in Winnipeg. That is also something we see time and time again: players who engage in challenging negotiations don't often stay with that team for long afterward. If we point again to Overhardt's other clients - Turris, Johansen, Dubinsky - we see an eventual trade on the horizon. We want Trouba to be a franchise player and the likelihood of that diminishes with each transition into the regular season.
I still maintain that he is not going to report to Jets TC after the world cup. What happens after that remains to be seen, but I'm almost certain that Trouba's camp will want the Jets to feel what it is like to not have him around. They'll have to sort out drills, pairings, line combos, and will be forced to have a closer look at other talent as possible short term replacements. Trouba's camp would be gambling in this being unbearable enough to get a deal done in their favour. Although there's also a risk of it being just fine for the Jets, without a holdout they have next to no leverage in negotiations.
A deal will get done no matter what, but it is clearly emerging that the kind of deal that's done is more important than when it gets done.