I think that, in all likelihood, Crosby will be a Pittsburgh Penguin until he retires.
If he goes elsewhere, his problem becomes: Which team that is legitimately contending can take his salary of $10M+? All of them have their core tied up to term & money already.
There aren't a ton of options available for him in that regard. However, we'd have no problem fitting him in money-wise. And if we need to make space, give San Jose a first round pick in return for taking Anderson's final two years.
Crosby would make this team a contender overnight. The defense would still be underwhelming and we don't have an actual #1 goalie, but at least the forward group would be more than good enough.