I would like it if Gai died, I think he should have instead of Naruto pulling a deus ex machina to save him. Him living made all of his prior words pointless.
I would be upset if Shikamaru died, mainly because I want to see him as an advisor in whatever new system is going to be put into place for shinobi.
And, maybe Kakashi too. He died once, dying a second time is redundant and unneeded. Plus, if he can make it through all this, he deserves to live.