One thing I'm sure didn't make those teams good is trading away all their veterans or trying to run the team into the ground. Notice that Chicago started improving when ownership changed and they added a few big Name UFA's.
I'm not sure you can invoke Chicago as some kind of "stay the course" example. That old skinflint did run the team into the ground in the 90s, but the scouts sowed the seeds of Chicago's 2010 Cup in the drafts of the 00s. They drafted Keith in 2002, Seabrook & Byfuglien in 2003, Bolland in 2004 (he was great for them in the playoffs in 2010), then of course Toews & Kane in 2006 & 2007. So the core of the Cup winner came from the draft, and they added the right pieces when the time came.
They got lucky that the old skinflint finally left this earth in 2007, just as that core was in place. His departure let better management see the rebuild through to completion.
So to sum up: the Hawks nabbed three quality defencemen and two star/superstar forwards from the draft to build around, then brought home the Cup with the right moves when that core was ready, which was three years after the last piece was drafted (Kane). If you believe the Habs have their three quality defencemen in Beaulieu, Tinordi, and Subban, and one star forward in Galchenyuk, plus a goalie in Price that the Hawks did not have, then we are still one forward short, and in any event, this core will not be ready until at least 2015 if not later; our defencemen are much earlier in their development than the Hawks comparables so it could be as late as 2017.
2013 is simply not our year, and trading veterans would be entirely consistent with that, and with building toward 2015-2017.