If he's rejecting a $8.5-9mil deal now, it's in your best interest to trade him for as much as you can. If it's not a trade and sign, you can circle back on July 1st.
I think $9.5mil is right at that level of move on. If he wants 10.5-11mil, you have to move on. $8-9.5 is a definite resign.
Looking at Vancouver's cap sheet next year, it's rough when looking at how to fit Jake in at $9-10mil. I don't think we want Kuzmenko back but I do think I would entertain Garland or Mikheyev. I think they'd prefer to keep Garland so Mikheyev might be more reason. Something like Mikheyev, Lekkimiaki, 1st* (Conditional on playoff performance) for Guentzel, 3rd would could be something I see working. That's right in line with the Horvat trade from last year.
Rakell-Crosby-Rust
DOC-Malkin-Mikheyev
Smith-Eller-Puustinen
Good enough to finish out the year.
Then I really push them to try to fit Yager and Lekkerimaki in next year. I'd look to send Smith to a team needing top 6 support. Again, Arizona if they are in it has an embarrassing amount of 2nds. Easy. I'd offer up Nieto, Acciari, Carter, Rudwedel, POJ, and Graves as well (with Graves being unlikely obviously) and try to get picks, prospects, or young players in similar situations (such as POJ for Dube).
Yager-Crosby-Rust
DOC-Malkin-Lekkerimaki
Rakell-3C-Mikheyev
Poulin-Eller-Puustinen
That said, we'd have an enormous amount of space in that case so you could chase a big fish or find better scoring support. You might...MIGHT...be able to swing a compelling deal for Huberdeau in this case.
Huberdeau, 1st, Dube for Smith+POJ (or sub Smith for Rakell or Mikheyev).
Adding 2 additional 1sts, Lekkermiaki, Dube, and Huberdeau would be an interesting way to revamp the roster.
Huberdeau-Crosby-Rust
DOC-Malkin-Rakell
Dube-Yager-Mikheyev
Poulin-Eller-Lekkerimaki