I would say that I think Detroit will not be in that same situation is because Ken Holland will not let his salary cap get out of control again. Hudler left them once before for more money (to the KHL(which really soured me on him)) and then he was looking for top dollar again when he signed in Calgary. (by this time everyone wanted him gone so it was no big loss) So he was just looking for the biggest payday he could find. When Filppula left, the going rate for a 2nd line center was through the roof and Holland's plan for the rest of the team (I believe that was the same year he went balls out for Suter) didn't have any room left under the cap for that going rate. Holland will not let the cap control him again, he will contiue to grow his own talent, pay them accordingly and if the time comes where they are just looking for the payday and they no longer fit in the team cap structure, that is when he will lose them.
BUT, by the time Nyquist, Tatar, Mantha and Larkin are all in their primes here, we will no longer have to contracts of Dats, Z, Weiss and Franzen. Plus the hopes that the Cap increases slightly every year will also help. By the time Ouellet, Sproul, Marchenko, Dekeyser are all in their prime, Kronner, Ericsson will be gone off the books or on their last small career contracts. Same goes for Mrazek, by the time he is ready for that elilte contract, s*** stain's contract will be off the books. I know Mrazek is a RFA soon, but I think he still has that one bridge contract he'll sign before his big one.
Holland has enough young talent spread apart from each other to where he probably won't have to worry too much about having 5-6 stars making top dollar all at the same time.
IMO, there are only two scenarios where he may lose ANY of his "kids." 1. They just don't want to be here, or 2. He trades them. Like I said, the reason's Hudler and Fil left were more to do with wanting (some say deserving) more money than Holland had available without crippling his team. Kenny will not let his cap get that close again.
congrats on being the only one to actually answer the question.