Yzerman is shrewd/stubborn enough to create a plan that makes it work. Further, he's shown himself adapt at changing his plans around those who don't buy in to his plan.
As nerve wracking as the negotiation periods for all our talent has been and will continue to be; Yzerman has done great so far managing the cap year to year while maximizing value. He'll find a way to move any and all of Filppula, Callahan, Boyle, Garrison, Stralman, and Coburn before being forced out of any of the core pieces left to sign (Kucherov, Johnson, Palat, and Drouin). He knows who his core is and will build around them moving forward. Bridge Kucherov and Drouin and talk Johnson and Palat into discounted deals (considering what he just signed Stamkos and Hedman for this doesn't seem unreasonable) and maybe we can keep one or two of the vets around beyond next offseason.
Expansion draft protect Stamkos, Palat, Johnson, Kucherov, Drouin, Killorn, Namestnikov, Hedman, Sustr, Koekoek, and Vasilevski. That is essentially the core moving forward (possibly keeping Stralman over Sustr). Yzerman talks his NMCs into waiving their expansion draft protection if he needs to. Las Vegas can only draft one player per team. No reason Yzerman can't make one of his salary dumps of necessity in to Las Vegas' best draftable options from the Lightning.
Sure, there will be downgrades filling in the holes on the roster and growing pains as more youth is injected in to the roster again to replace departing veterans. Losing Bishop seems suicidal. Sacrificing the veterans to pay the youth...good GMs find a way to get this done, it's just business. Yzerman has been a good GM to date. He'll figure it out.