At the end of the day, the point of a rebuild is to acquire elite talent. Why? Because you will need elite talent to win a cup. How do you acquire elite talent? There are four ways, lets explore the possibilities of the red wings acquiring such a player
1) a trade
2) free agency
3) the draft
4) a miracle (kind of ties into the rest)
1) Trading for an elite talent can only really be done by trading away an elite talent of your own... a one for one exchange. Nobody in their right mind would trade an elite player for a bunch of parts that kind-of-but-not-really sum up to an elite player. The red wings do not have an elite talent to trade, other than Zetterberg who is very old and thus has significantly diminished value. A trade for elite talent is not possible for Detroit.
2) Elite talents don't often hit free agency, and when they do you often have to overpay them a bit in the open market. Unfortunately, Detroit's cap is so mismanaged that they couldn't sign an elite talent in free agency even if they wanted to. What if Karlsson ditches Ottawa? Tavares ditches NYI? Doesn't matter, cant afford them anyway. Free agency is out of the question for Detroit.
3) The draft. There is a lot of luck in the draft. There are two ways to maximize your luck: Acquire as many draft picks as possible, and draft as high as possible. Detroit has done literally the exact opposite of this. We have traded away picks in order to acquire decent players in order to keep us from missing the playoffs and drafting high. Its laughable when you think about it. Due to Detroit doing the exact opposite of what a team must do to acquire elite talent, we have not been able to acquire one this way. Fortunately we are starting to slide in the standings despite Holland's best efforts, which means we will have a greater shot at picking very high. Winning the lottery is our best shot at getting an elite talent, which is starting to become more and more likely (still unlikely)
4) A miracle. The core of the strategy in Holland's master plan. It ties into all three of the aforementioned ways of acquiring an elite talent. Make a trade for a young player that miraculously turns into a superstar - like Brent Burns. Sign a cheap free agent that turns into a superstar, I don't have a good example but I guess Chicago signing Artemi Panarin. Or a miracle in the draft which we very are familiar with... players like Zetterberg, Datsyuk, Jamie Benn, etc. Another type of miracle would be finishing just outside of the playoffs and then miraculously win the draft lottery, like philly did last year.
Ultimately, Holland's biggest mistake was failing to recognize when our cup window closed. He never did that, and as such didn't change his management strategy to a rebuild. He kept managing the team as if we were full of elite talent and cup contending like we were for a decade and a half.