The reality of the situation is we need to try and turn some of our assets that are up for big money contracts into assets that are undervalued contracts with team control left. I don't know how you do that other than identifying a team with a competitive window that fits that need.
With that said, I think if you could get everyone in the same room, I truly think the best fit would probably be some kind of three-way deal with Calgary and Florida. Calgary probably sees a need to add forward depth and they can deal from a position of strength on D (especially if they're adding a guy like Alex Yelesin from the K, which it seems like they are) ... Florida really seems to be a good fit (player and team) for Trouba and Winnipeg could use a team like Calgary to bolster their D corps with the loss of Trouba.
Florida gets: Jacob Trouba, James Neal
Calgary gets: Vincent Trocheck, Matthieu Perreault
Winnipeg gets: Noah Hanifin
Add picks/prospects as you see necessary to make the deal work.
Why for Florida? They have the cap space to add Trouba and have long been reported to be a team interested in acquiring him - the fit for the player is there too, as Trouba wants to be in Florida with his girlfriend. James Neal is an albatross for Calgary, but he might be a better fit on the wing in Florida for a team that would need to fill a hole on the wing when Huberdeau goes back to the middle to fill the hole left by Trocheck. Gives them a top six of Dadonov-Barkov-Hoffman, Tippett-Huberdeau-Neal and you can still add spare parts in FA with your excess cap space (they should still have around 6-7 million left over and their only real guy they need to give more cash to is Hawryluk)
Why not for Florida? Maybe they're not comfortable moving Huberdeau to the middle and then maybe Neal is redundant, especially since you can spend your money in better ways (like finding a better option than Hawryluk for your 2C)
Why for Calgary? They really seem to need add forward depth and Trocheck is the kind of cost effective 2C that will present them with the ability to have an easier time resigning all the big ticket players they're going to have coming up in the next little while ... Tkachuk/Rittich as RFA this year ... Brodie/Hamonic UFA and Jankowski RFA the year after ... Perreault gives you some bridge depth that you can afford in the interim to keep your team's top 9 solid, especially if you let Bennett walk as another cost-controlled measure.
Why not for Calgary? Maybe Hanifin isn't the piece they want to give up on D and they're not sold on their ability to retain Brodie/Hamonic the year after next and would rather keep the guy they have secured for longer term.
Why for Winnipeg? The biggest asset you gain here is the flexibility to retain your players in a cap crunch and offer your current roster an opportunity to gain a bigger role. Hanifin is a big add for a team that just lost Trouba.
Why not for Winnipeg? I'm not sure. Maybe that's a sign this trade isn't as good as I think it is but I already typed all this **** out and I still think it makes decent sense so here we are.