I still remember that '96 season. I'm not even going to lie, I drank the Kool-Aid; after Penny held the fort down while Shaq was injured, I said good riddance.
And yes, technically, with no state tax, Shaq would have made more w/ Orlando, but the damage was done.
Whether Shaq stayed or not, they wouldn't have won the chip while the Bulls were re-establishing their dynasty. Plus, Penny's knee injury occurred while playing with Shaq, Nick Anderson's confidence was shot (though he still had a solid career) and Dennis Scott was a one dimensional player. And don't let the 30 for 30 fool you, they had no bench whatsoever.
Still, we had that '97 Heat series where Penny went 42, 41, 33 in games 3-5 respectively.