@WestchesterFrugal - I can relate to your post to some extent, I work on Wall Street too and live in a nearby community. I myself am not an Ivy Leaguerer but a great many of my friends are.
I bring my lunch to work because its healthier and at an average of $11 a day, 5 days a week 48 weeks a year that’s $2640, making my own lunch probably costs half that, I just don't care what my co-workers think, I usually make fun of them for going to Pret or Cosi or who knows where... We can all afford it, I tell them flat out I would rather keep the cash and we move on. Now when some quits/retires or it’s a birthday lunch of course we go out, that is no longer about being frugal or being healthy it is now about being social so the savings go out the window, but that is the oddity not every day.
We have live in help, I have 2 young kids and we love the extra set of hands, our Au Pair is awesome, I don't care what anyone here says she is family and we will keep in touch with her forever.
I believe in public school personally I think it builds character, we live in a great school district and pay the taxes to boot, you make enough to send your kids to private school that’s you choice, but understand the impact of the expense, and ask yourself what it buys you... If your kids are smart enough they will make the Ivy Leagues anyway, private school is just a rich person’s way to buy their way in especially for legacies and that is what it is. So ask yourself if you are doing it for them or yourself, I'm not judging just asking you to look at your reasoning, I know lots of friend who have changed their minds on how they feel about this…
Country Clubs, well this too is your choice, if you enjoy it stay a member, me I don't golf, I'm more of a skydiver personally, well not since I have kids. I have plenty of friends and don't feel the need to be a member for social interactions, if you like the experience and think it is worth the money keep it up, if not no one will judge you for reallocating the fees to other hobbies you enjoy more.
The rental house, real estate is what it is around here, if it is not causing you stress then keep trying to unload as the market moves.
I have a landscaper, plow service, pool maintainence etc... Time is more valuable to me etc...
My wife loves to shop, however she is more interested in getting deals than anything she will buy her Kooba bags but only at Marshals or TJ's when they are half price and then she wants to sell them on eBay for a profit, Louis only when she gets an employee discount from someone she knows. My wife will negotiate sales tax with NYS. Craigslist has remarkable deals, we never pay full price for anything.
So here is the only part of your post that really concerns me, I didn't really run your numbers and confirm the math or anything, however it is clear you make substantially more than I do by a multiple of over 5, I am a software engineer you are clearly closer to the money some form of trader or banker is my guess. Here’s the thing our net worth’s are about the same give or take a few hundred thousand, but our assets and liabilities are off by millions and so are our expenses. We are also in our late 30’s
I hang out with the same people as you do, maybe literally even some of the same people (not likely though) I've been around Wall Street for the last 10 years or so at many of the major IBanks.
There are lots of things in your life you can change if you want to, the question is do you want to? If so then you have the means to do whatever you want. Personally I'm not so Mustacian as much as I am fiscally responsible and save more than I spend. We just live way below our means. I like a lot of what MMM has to say and agree with a lot of his ideals, but in the end I am far too much of a consumer and capitalist to ever be considered Mustachain.
Feel free to private message me if you want to talk in more depth offline about anything. And by the way, your original post took a lot of nerve on this forum; most people here have no idea how to even think along the lines of the numbers you are talking.
Good luck,
-Mister FancyPants