Taking some risks

canucks accept if you put a 6th-7th round pick in return

Penguins decline the VAN trade, it's a non starter.
4.75 for a 3rd-4th line tweener isn't happening. Let alone buying out Rakell who is a better player for that crap.

It also costs far more to dump anyway. 3.4x2 got a 2nd just yesterday. 4.75x 2, you are adding.

As for the OTT trade. Smith put up more points than Joseph in a bad year. Why would they want to down grade.
Smith is the better player, even at 33. On top of it his contract ends this year and it's done. They aren't stuck with that cap hit for another year.

It's best to just let the cap hit come off the books. Pens probably trade him at TDL anyway for a small return. As the team above isn't making the playoffs.

Sens aren’t in any position to get more expensive in their depth