I feel like if Nylander was willing to sign a 8x$8.9 contract, Toronto would probably just keep him at that price. It's only a $2 million increase from his currently contract and for 8 years.

Very valid point. Maybe the biggest difference is that the $8.9mil goes a lot farther in Nashville due to state taxes compared to Toronto. I think Nashville ranks like #6 on lowest income tax for all the teams, and Toronto is like #23 or something along those lines. If it is like 5-8% difference. Like, 8% on $9.0 mil is $720k. So to make the same in Toronto, he would need to sign for $9.7mil per season. (Roughly)

Nothing here will ever match what Nylander brings. This is not realistic it's a win for Nashville

The taxes argument has basically been debunked. Especially for the Leafs - they tend to give their stars all of their money up front (signing bonuses) which is worth $. Plus endorsement opportunities are higher in Toronto