If you have your own business and have a good accountant, you should be able to find some ways to incur major losses. Look at that other NYC resident Donald Trump, he's done very well with all of his bankruptcies. Seriously though, the more you have the more you should be able to deduct. It's not that hard. You just need to make it sound reasonable. Want to buy a yacht and sale around the world with your family? Probably can't deduct that. Did you make $20,000 from a book that you wrote about the experience. Well, then, you might have a case.
As far as NYC, you are definitely rationalizing. I live in Montclair and retired over the last year on over $4.5 million in securities and the like. I also have a house worth over $1 million with over 3,000 square feet. I could easily walk to most things I wanted to do and if walkability was a prime factor, I could buy another equally nice house that would be in an even more walkable area (we chose to live on a hill for more privacy, the view, and the architecture of the house we bought).
I'll be the first to say there are extravagances living here… Like the taxes, about $25k a year. But I have two kids and they both go to public school, so it's a LOT cheaper to pay the taxes then to send them to private school (not to mention, take deductible, see above about losses). I moved here when I was employed in the city, so I played the arbitrage game, living in a less expensive area and commuting to a more expensive area. My kids' friends are from a diverse economic background, which I think is important for them, but many of them are from families where hard work has led to financial success. That's a worthwhile lesson right there. I grew up in a rural environment where such lessons were few and far between, so I think that's important. Will they get into good schools if they get good grades in their (public) high school? Oh ya, they will, no question. So that's worth it right there. Did I join the country club? No. Did I join the $7,000 a summer swim and racket club? No again. Am I still seeing my contacts in the city now that I'm retired? No. And why should I? I am retired. They have to live their lives, I live mine. I garden, I read stoic philosophy, I have my own projects in art and music, I go to the gym, cycle, and run. After all, I'm retired at 49.
By removing yourself from Manhattan you will find yourself needing it less and less. Otherwise you may yet find it impossible to retire. Maybe that's fine. 35 is pretty young. You can start another business. But then again, it could also go bust and cost you a lot of money…
As for that bodega. Stop shopping at that bodega. That's insane. I've bought produce at Fairway in the city before they opened up out here. It's much cheaper there and a bodega is by definition full of rats. You can also order Fresh Direct. Even Ronnybrook is $5.49 a half gallon and that stuff is crazy expensive. So reality check, don't shop at the bodega again. Ever.