They really should've figured it out by now. And by that I mean not have the same type of feel of disappointment and same type of losses happen over and over again, year after year.
If this team doesn't sniff at the wild card this year, I don't know if they will ever win with this core. At some point losing just becomes part of your identity.
I mean, how much can you really do with the roster? Sure, they could have someone good at filling a specific role instead of Perron, and swap Giroux for someone closer to their prime, but most of what you can do is more or less lateral movement, and even if there's an upgrade to be had somewhere, is that enough to push them over the edge? Probably not.
Now with Ullmark signed, the core of the team is taking bulk of the cap space.
Next step is starting to shake things up for real. Explore if there's any trade possibilities for Chabot and Norris to begin with, even if the return is crap.