The advice you are giving is terrible from a real estate investing perspective: big (much more than needed) house, nicest on the block, in a (relative to surrounding) undesireable area with high carrying costs and horrible reputation for schools, which will be very difficult to sell eventually - who do you think would buy a huge 7br home with the worst schools in the general vicinity?
Maybe I should have mentioned that residential real estate provides almost 30% of my household income (which is in the top 2% nationwide). Or do I have to buy a $4000 purse and the "right" shoes before you'll listen to anything I say?
Since you bought a new $2 million house despite not being able to sell your other $2 million house, and have since been renting out the original $2 million house for no profit while shelling out thousands of bucks to have someone mow your tenants' lawn--not to mention, you don't even seem to realize that it's much easier to sell a $1 million home in a nice or great area than a $2 million home in a fabulous area, simply because there are far more potential buyers and most of them are less snobbish than you and your business acquaintances--I am not sure on what basis you feel like a more competent real estate investor than me or the other real estate investors here.
Here's how we got to this point in the conversation: You claimed that reducing your housing expenses was not in the cards so long as you stayed in the Northeast because
according to you, in your area, there was probably no such thing as an adequately large house[/i] (i.e., as defined by you, at least 5BR and 4000-ish square feet--your current house has 3k above ground and 1k below) for much less than your current $2 million house--certainly not for anything close to just $1 million.
So I provided you with links to several such houses that are for sale in your area right now, at prices from $965k to $1.4m. And hey, my apologies if one of them had two more bedrooms than your stated minimum--I guess I erroneously thought you might be able to use them as, for instance, a home office, a guest room, a gym, a library (do you guys read?), etc.
Having more space than you need is a problem only to the extent that it costs more;[/i] the 7BR house is half the price of yours and has solar panels to keep utility costs down, so I thought as a finance person you should be able to perceive that the problem normally posed by excess space did not exist in that particular case.
But
instead of interpreting these listings as EXAMPLES proving that you were quite possibly incorrect[/i] in assuming that you couldn't get 5BR for significantly less than what you're paying now--that is, instead of thinking, "Hmm, maybe I *could* get the large house I need for much less money--perhaps I should keep an eye on local real estate listings"--you deployed your vast real estate wisdom to sniffily dismiss a couple of those houses as being in "secondary" areas with "the worst" schools in town.
That, to you, apparently proves that your assumption was correct and thus no further discussion need be had about reducing your housing expenses.[/i] If you were looking for information instead of looking for ways to justify decisions you've already made, you would not have responded that way.
By the way, even setting aside the fact that school districts for $1m+ homes in your area are quasi-irrelevant because most people at these income levels send their kids to private school, "worst" means little or nothing in this context. You might as well dismiss as "the worst" the person who came in last in figure skating at the Sochi Olympics; that person is still one of the best figure skaters in the world.
Oh, and FYI, my two fastest-renting and most lucrative rentals (in terms of what they bring in vs. what they cost) are in not even secondary--heck, not even tertiary areas in my city. Because guess what?
People who rent (or in your case buy) at lower prices have lower expectations in terms of snob appeal.[/i] I'm telling you this because you seem to have completely forgotten how people with less money than you think and what criteria they base their major financial decisions on. Every time I put these places on the market they rent immediately--the last changeover had 12 days between tenant A moving out and tenant B moving in, and the one before that had 0 days. And that's not because I have low standards for tenants; apart from the rich Asian grad students I sometimes rent to, who have no US credit and thus no credit scores, I've never rented to someone with a credit score below 700.
But all you seem interested in doing here is rationalizing decisions you have already made.[/i] You have decided that there is no point reducing your housing expenses; you dismiss all evidence to the contrary. You have decided that continuing to buy expensive crap can be rationalized as a business decision, based on
your sad assumption that people won't like you as much if you don't buy the same crap as them[/i], and thus will choose not to do business with you. Then you dismiss evidence to the contrary, even when it comes from other rich people or from a self-described New England blueblood who travels in much richer circles than yours.
It is interesting you are able to make such blanket assumptions when you have no idea how much my current house is worth or what the size of the yard is
You told us on this thread that it was a $2 million house and that one of the listings I linked to, which had 1.9 acres, had more acreage than you. If that's not true then I am indeed talking based on false information, but that's because of what you posted, not because of any assumptions I made.
In the world I work in, people want to do business with people they like, and 90% of people like others who are like themselves.
So you could say that assimilation is a business decision to some degree.
Notice how your business associates--I'm not going to call them friends, since by your description that's not what they are--don't retire early? You cannot BOTH keep designing your life to match other people's lives AND retire early, unless the people whose lives you're aping themselves retire early.
And given your sniffy dismissal of million-buck homes with insufficient snob appeal (and that is your complaint, much as you try to dress it up as an investment decision: you can't accurately judge the investment value of a $1m home based on the expectations of people who buy $2m homes)...anyway, given that, I doubt that you will be able to bear living in a "secondary" area (or belonging to a secondary country club, etc.) when you retire, because
you have conditioned yourself to experience that as a loss of status, and status (a.k.a. the opinions of people who aren't even your friends) is something you value way too highly. That means you will feel obligated to spend massive amounts of money in retirement, just as you are spending massive amounts of money now.
So again,
because you define "having it all" as keeping up with the Joneses (aka buying whatever expensive crap you have to buy to ensure that superficial people you're not even friends with continue to think you're worthwhile), the answer is NO: You cannot "have it all" and retire early. To retire early, you'll need to change your definition of "having it all."