To chime in on the Heaton/TZE debate:
When talking about roster values, I don't think it's so much discounting the Wings' accomplishments over their run, I think it has more to do with the fact that you can't really properly evaluate an organization over a huge period of time. Management teams come and go, dominant play styles in the league come and go, the structure of the league itself changes (salary cap, draft lottery) etc. You kind of have to evaluate things in blocks of 5-10 years at most. So in that sense where we are now is not 'just' a result of our greatness. There have been many stumbles and counterproductive moves in the past half-decade. Where we are now could be very different had those 'lost' years played out differently in terms of drafting, free agency, trades, etc., i.e. if the rebuild had started earlier.
It's interesting that the teams mentioned in your exchange have been Winnipeg, Chicago, Tampa, and Nashville. The first three have taken the path us scorched earthers advocated for years ago, that you needed to be the worst so that you could be the best again. It's hard to argue against the value of that approach given the success that Chicago has enjoyed (and you can't ignore it if we're talking in the context of Cup wins), the success that Tampa has enjoyed, and that Winnipeg is currently enjoying. And the latter 2 show no signs of slowing down either. But on the other hand, Nashville has taken an approach much more similar to what the Wings have. Regarding the draft, they never had a top 5 pick as far as I'm aware. Yet they have been contenders for several years now.
So 'scorched earth' and 'steady as she goes' can both lead to contention given a smart management team, IMO. I think it has more to do with evaluating where your team currently is to determine the correct approach. That's why I don't favour a scorched earth approach anymore, that ship has sailed. The time to do that (which is when I favoured it) would have been when this team was overflowing with bloated vet contracts and there wasn't much of anything to boast about in the under-25 department. The only 2 hard decisions in a scorched earth scenario would have been Datsyuk and Zetterberg, the rest would have been easy.
That was Holland's major flaw in my eyes, that he didn't bite the bullet when he should have and wasted 3-4 years treading water with no real plan for the future. Ironically he ended up in essentially the same scenario that a scorched earth approach would have put him in, a blank slate. So that's why I call those 3-4 seasons 'lost years'. However I have been pleased with Holland's work over the last 1-1.5 years. He has improved his drafting tremendously and has so far mostly avoided bad contracts. For the first time in a long time, our salary cap outlook actually looks pretty good in the medium-long term.
Holland's legacy is set in Detroit, no doubt about it. The 2012-2016/7 years are just an unfortunate blemish on an otherwise stellar career. And he has once again started to show the wisdom and savvy that made his so successful and legendary in the first place. That said I am still hoping Yzerman will become this team's new GM after this season. Only because I think he is skilled like Holland (I mean, he was basically his apprentice), and that he will be able to stay in the game for a long time because of his age. I also think he is a better cap manager. It's time for Stevie Y to come home and take that torch to lead Detroit into the next Golden Age. He'll be coming in with a solid foundation to build upon, just like Holland had way back in the early 90s.