I actually think Chicago is more or less on the right track as is. Getting Dach was a coup, and they have some nice young D well on their way. Kubalik was a nice find, and drafting a kid like Reichel was astute as well. That's just off the top of my head as well, I'm sure there's more to it than that
They haven't exactly been lights out in recent years, even with their current core, so I'm not convinced that it's necessary to have a firesale to truly bottom out. (I realize there were extenuating circumstances there, with Crawford's injury issues, a suspect D, etc etc)
If it were me, maybe make a change from Bowman, sell off guys like Strome and/or Murphy over the next couple years (and any of the vets who decide they'd like to move on). But I wouldn't try and force out anyone (they've earned the right to stay or go as they please), and there's inherent value in their winning pedigree and ability to help insulate & mentor the kids... not everything is just about accumulating *shiny assets* imo