Seems like some revisionist history going on here.
Had the Wings gotten past Chicago a few years ago, it still would've been a very rough path to a championship. Not impossible, but FAR from a given. That season felt very much like a "lightning in a bottle" kind of run with some of the youth, which may have continued onward, or may have run out of gas. No real way of knowing.
As for last year, Tampa was the best matchup they could've had in the first round. It was a close defeat, but Montreal would've had them for lunch, and New York wasn't all that far behind.
The Wings, at minimum, need another top 4 defenseman to really contend for a Cup. If they have any aspirations of ever being a favorite again, that needs to be a top pairing defenseman, and they need to throw in another scoring forward to boot. But for all we know, they might have one or more of those players in the system...I'm just not optimistic that they'll pan out in the next 6 months.
Ideally, they deal a forward or two for a defenseman at the deadline, but there's not exactly a track record for pulling those off lately, so we'll see...