Just to note about the aging core - we need only look to the Bruins to see quality older players can still carry a team to success but only if the team around them is built properly. There are enough similarities between the Hawks-Bruins that we could look to them for ways the Hawks could succeed sooner rather than later.
Bruins' original core is actually older than the Hawks; Kane is better offensively than any of their core; Toews had a resurgent year that is on par with Bergeron so we have to hope that continues; and Keith is at least as good as 40+ Chara (I will fight people on this). The Bruins even have a bad contract with Backes like the Hawks do with Seabrook and an aging goalie but who is still great. Bruins missed the playoffs two seasons sandwiched by 1 and then 2 years of early exits from the post-season, so like the Hawks currently, they went through some trying years.
So, what did the Bruins do to be successful? They built around their core primarily through young players they developed themselves (forward and defense), key minor role position adds (off seasons and TDL), and they have a great 1-3 offensive line + checking line that seems to be the most successful line roll-out in recent years.
The Hawks have been going the rebuild on the fly method for a few years now, so it's good to have examples of it working out for a team. The Pens and Caps also did this in some regard, just less missing playoffs and more 1st/2nd round exits. Not a lock, but possible.
- L_B_R
The Bruins have a younger , bigger , faster more mobile team including their defense.
Also tuka Rask, hasn't been injured unlike crawford who has suffered 2 concussions.
Keith and Seabrook are both well past their hay days and neither should be playing in a top 4 role .
Kane and toews should not be paired together because it limits Chicago's offense.
Also Boston has had years to rebuild their team, Chicago rebuild basically started last year and your 2 core players are both turning 31 years old.
I'm sorry but Boston has a example is just bad example.
You could compare Pittsburgh to chicago . Both teams have aging players , bad contracts and lots of needs.
We can both disagree , but I'm just being realistic looking at Chicago's overall depth , needs and skill.