Hi, I'm new here (and, ironically, no longer living in NY) but one thing that doesn't seem to have been mentioned vis-a-vis wine prices is that, while wine markups are ostensibly to "subsidize" food costs and other operating expenses, those 20% tips on $300 bottles of wine are also "subsidizing" a higher standard of service. We can all complain that servers at 2+ star restaurants (except Superiority Burger and Parm) make more money than most adjunct professors - but the fact is that a big part of the reason service standards are so relatively high in New York is precisely because servers make a lot of money from tips on expensive bottles of wine. Those tips balance out the slow nights, and attract a pool of skilled, smart, experienced, and engaged-and-engaging servers to those restaurants.
Obviously this doesn't apply to most restaurants (but neither does the question of tipping on $200+ wine), and it doesn't necessarily even apply to most servers at those restaurants. But those occasional $500 tips definitely, at the margin, keep some servers around who might otherwise decamp for other work.
(All of which is not to say that an alternative system - whether a standard "service fee" or, better, to just build that compensation into menu prices, at which point it's just up to management to determine, right or wrong, where labor costs are best allocated - wouldn't be preferable. Just that, in the current system for many places, this is what's up with a lot of those 20% tips on wine.)