It looks good roster, although I'm not sure about UPL yet, and even Comrie.

Capitals decline but the rest is pretty good

I laid out my reasoning

With all respect to Olofsson, it's not the production we'd be worried about with Oshie. In theory, its a great deal from Washington, to get Oshie's declining contract off the books and pick up a decent wing option, but for whatever reason, the team does not function without Oshie. The power play looks futile more often than not when Oshie is out, and the team lacks something (energy maybe?) when he's not in the lineup. I have to think the Caps would be inclined to disregard a trade of Oshie at this point, especially with the team still not at full strength.

This AGM is next year

All the more reason to keep him, if Backstrom truly is intent on returning to play. They'd likely have to move out Eller to make the cap work, but it is definitely preferable to trading Oshie. I fear what will happen when he retires, the team doesn't function as well without him. (Also I think Buffalo may end up in his NTC, though perhaps not. He's said he doesn't want to leave Washington and want's to retire here, including killing any possibility of getting taken in the Expansion draft, but it is only a 10 team NTC and I can easily think of 10 places less appealing than Buffalo)

Again, this is next year. Look at what I wrote in the trade notes and look at how many UFAs you have. You have one defensemen under contract

Correct, but that can be remedied without much trouble. With Eller's 3.5 coming off the books (as well as Brown's contract, unfortunately), as well as Alexeyev being an RFA who won't likely see a huge payday and Iorio likely being NHL ready, the money Washington saves through different contracts leaving should allow them the room to bring back Orlov and Jensen if they choose to, without much worry. The money that could be saved by dealing Oshie won't be worth the loss in play from the rest of the team, especially when you could instead move someone like Mantha for less of a detriment to the team. Plus, if Backstrom follows the normal path of players who get the hip surgery he did, he'll likely get 20ish games at the end of the season and then retire (like Jovanovski), it'll clear up more than enough space for everyone to return without issue. Moving Oshie at this time just isn't the move given the likely downturn in play from the rest of the team.

While on paper it makes sense for the caps to move Oshie and get him off the books, there is IMO a 0% chance they do. The point production from him and Olofsson will probably be the same, but as much as people like to pretend it isn't a thing no one can replace the leadership and glue he brings to the locker room. The Caps have also been incredibly good to their players, and even though Oshie's NTC is modified I doubt they even think of trading him unless he asks for it -- he and his family have been super active in the community and have been in DC for a long time, I doubt he would waive anywhere. Everyone outside of DC was shocked when the Caps didn't leave him exposed for Seattle -- don't have it happen again when he retires a Cap!

Idk... you're packaging 3 players that have been struggling this season (I know Mittelstadt has been producing decently but I'm not sold on his 5v5 play) for a solid defensive defenseman + a pick.
Don't really see how Winnipeg would accept this unless they're blinded by Mitts' draft position/whatever upside is there.