I think the biggest distinction is one GM (Yzerman) said be patient because it's going to be a long rebuild.
8-10-2 looks like well on their way to select some more nice prospects.
Whereas the other GM (Sens) announced the rebuild was officially over and they are ready to compete. 8-11-1 doesn't look too promising at competing to me.
So you're basing this purely on team PR? The reality is that right now Detroit and Ottawa are both in roughly the same spot. And while Detroit does have a better prospect pool, Ottawa also has more young players playing in the NHL and contributing; essentially, they're where Detroit will be in 2 years. And technically, Detroit has been in the basement even longer than Ottawa, so it's not like Ottawa had more time to rebuild.
Mind you, this isn't a defense of Ottawa's rebuild, which I think has been pretty mediocre. I just don't think Detroit is in position to criticize.
Why do they need "significant" assets in return? I'm sure the goalies will return some nice assets however. Playoff teams love depth, especially cheap depth. Yzerman can retain any amount of cap depending on the return.
It's true that Talbot could return something if he continues his good form, though the market for goalies is rarely that rewarding. Chiarot or Petry could probably return a mid-round pick with retention, despite their poor play. But Copp and Compher have too many years left, and Kane and Tarasenko just look cooked. The trade deadline won't do much for Detroit.
You say Wings need 4 good top 9 forwards and a few dmen and a starting goalie. Have you seen the prospect pool? If you are a DRWs fan, there's plenty in the system to be excited about. It'd be redundant if I list them all, but many look very promising. There's young players in this system that should be on the roster right now, but Yzerman is over ripening.
Do you follow Detroit's prospect pool? I would say it is underrated, but they are touted by almost every reputable NHL site as being top 5 in the league. So I guess they are not really underrated, but probably not followed by casual fans. It'd be disappointing if those players don't hit; Danielson, MBN, Cossa, ASP, one of Lombardi/Mazur/Buchelnikov/Kiiskinen. etc.
I don't think you realize just how difficult it is to replace AND upgrade 35% of your roster with purely prospects in only a couple years. I actually really like Detroit's current prospect pool, but it's completely unrealistic to expect any development system to achieve this.
Let's be optimistic and go along with your scenario: let's say all those prospects (Danielson, MBN, Cossa, ASP and one of the rest) hit and are good NHL players within 2-3 years. Even in this scenario, Detroit still winds short a couple top-9 forwards and one top-4 Dman. And that's a big problem, because it's not like the team can rely on having a lot of elite offensive talent to compensate for a lack of depth. Even with all of Detroit's current most promising young players integrated into the lineup, this team isn't close to being a contender.
And that's ignoring the fact that things never go that smoothly in a rebuild. Detroit core players will inevitably experience bumps in the road, injuries, regression; that's just reality. And we haven't even touched on the fact that Larkin by then will have entered his 30s, and will likely regress (players that rely on their speed as much as Larkin rarely age that well), leaving a big hole at #1C that no current Detroit prospect can realistically fill.
I think when the time is right, Yzerman will use his special trading skills and go hunting with some draft capital. The time isn't right just yet. He is letting the prospects marinate. Like you said above, placeholder contracts don't expire for another 2-3 years.
Yzerman's special trading skills don't seem to have survived the transition to Detroit unscathed, because his trade record has not been that impressive in the past 6 years. Aside from the (admittedly solid) Debrincat acquisition, it's been mostly low-stakes garbage-in, garbage-out trades. The fact that he only added a single good non-draft piece to this team in 6 years is underwhelming. It's also part of the reason why this roster has so many holes right now, too many to be filled purely by prospects.