I'd do:
Dvorak
Hoffman
1st Florida
One of Harris/Barron
One of Beck/Roy
for PLD
Dvorak has two years left at 4,45M$ AAV. He had a difficult seasons since he's with us, but than again, everyone had it rough on the Habs in the last two years. He was solid in Arizona tho and might be able to turn it around. He'd be a "band-aid" for Winnipeg's center depth
Hoffman is in his last year at 4,5M AAV. By now, everybody knows what's the deal with him, he's pretty much a cap dump. Useful on PP, but a liability in defense. If the Jets tanks this year, they could try to flip him at the tdl. If they don't do it, Hoffman is gone at the end of the year anyway
1st Florida will either be 31th or 32th.
Harris and Barron are solid defenseman prospects. They're not stars, but both of them will end up with a job in the NHL for sure. If Winnipeg take the rebuild route, they could be nice pieces
Both Beck and Roy are incredible prospects. IMO in the depth chart, they are behind only Hutson and "maybe" Mailloux. Beck is a great two ways center. Roy is a super solid winger, and he can do the defensive plays too, à la Toffoli
This trade give cap space to Montreal, along with a solid 2nd center to play behind Suzuki, and the cap space to sign him
Winnipeg get a kick start at their own rebuild