On re-signing: with (approximately) Matthews at $10M, Nylander/Marner at $7M, Rielly and Andersen at $5M, we're not going to have much to spend elsewhere, and a scoring winger is surely the role easiest for us to fill internally, both now and a couple of years down the road when guys like Bracco/Timashov might be knocking at the door.
On trading: I think, if not for playing in the Atlantic, we'd see ourselves as more of a bubble team in transition rather than some solid playoff contender. As difficult a sell as trading a player like JVR or Bozak while sitting comfortably in a playoff position may be, and as much as a GM never wants to send a message that they're lacking in faith heading into the playoffs.... I'm just not convinced it makes all that much sense to hang onto expiring UFAs for what, if we're being honest, is not likely to be a very fruitful playoff run. If you frame the question in terms of how much of a difference will JVR make in a playoff round vs. how much of a difference an additional pick might make long-term, it's a pretty easy decision for me.
I mean, if we didn't have JVR, and did have an extra 1st round pick.... would we trade that pick for JVR to load up for a run at the Bruins/Lightning? I wouldn't. It is undeniably weird to move a player like JVR before the playoffs, but it's also weird that we're 19 points ahead of the next-place team in the division in February.