Given what players were available, who picked who, etc, etc... yes, there are multiple timelines, but it seems fairly clear the Wings lucked out in not being hurt nearly as much by losing all those draft positions as they could have been. To me, 2020 is the only one that really stings, because A) we were by far the worst team in the NHL and drafted 4th, so that sucks just on principle, and then B) we missed out on Stutzle. But then you have the 'multiple timelines' factor come into play again... does Detroit even pick Stutzle if they had #1 or #2?
Losing 8 spots in 4 years certainly sucks, but it's not as damaging as a lot of people think.
Comparatively, what really bit Detroit in all these years was the poor drafting with the top picks they had in 17 and 18. Rasmussen is maybe finally becoming a player, which is great, but Detroit passed on Necas, Suzuki, and Hughes in 17/18. That stings more than missing out on the likes of Lias Andersson, Casey Mittelstadt, Barret Hayton, and Alex Turcotte.