Wine has played a central role in the Bear. Bear's mother is a raging alcoholic among other things. His sister tries to hide the wine bottles from her. Bear attends 12-step meetings. The family in total is an out-of-control emotional mess and liquor and substance abuse only add fire.
So the writers are in a tough place since they have insight into families like this - including one with a suicide.
But back to the restaurant, yes they would be serving wine paired with each dish. And people who can afford $300 meals would demand it. The Bear is short on figuring out their profit centers: The Wine and The Dessert. Ergo, they are broke all of the time.
So there we have it, opportunities in Season 4. But just think the uneducated and moronic Richie will become a wine expert. Perish the thought... Thank you. Am following....