When it's time to move Jake, you're pulling the plug on this era's life support imo. You're not improving in the here and now with a Jake trade, and I say that as someone who thinks Jake's a purely sidecar winger.
You're not getting somebody like Bratt or Mercer for Jake, especially since they're from a team within the divison. You're not getting a prospect with enough upside who is NHL ready to make a difference in the two years Sid has left. You're not getting a Neal for Hornqvist move that changes the style of the team in a way meaningful enough to make up for the probable production drop off.
They're 100% gonna hold on to him and re-sign him to some dumb contract (too long, too much money, too restrictive a NTC), which they will be cratering the value of the one, single valuable asset this team has anymore as the organization's teetering on the brink of a rebuild.