StuckinCT -
Free advice, so worth your admission fee to the board, but here's a few thoughts:
Like you, I'm 44 and have a couple of kids who are jobs #1 and #2 in my life. My net worth isn't yours, but we're comfortable by any definition.
Some years back, I moved across the country to take one of those high stress/high pay jobs and my wife and I found ourselves choosing a neighborhood. We faced down the trade-offs about lifestyle, neighbors, cost of everything and what we wanted for our kids. My conclusion:
So much of our sense of contentment as adults is about outcomes vs. expectations that were set in our youth.
I grew up without a lot (but enough). The only time I spent at a country club was the 7 years I worked at one. I had a job of some sort nearly everyday since I was 13. My first car was such a piece of crap that I tied an old boom box to the head rests with twine to have music ("you might be a red neck if..."). I borrowed to go to college and worked my tail off to pay it off. I never expected to make much money but wanted to achieve stability for my family and (thankfully) was able to achieve that.
I'm a very contented person because compared to what I was trained to expect in my youth, I'm doing great. I'm confident because I've handled most things on my own (with my spouse). I've never relied on OPM to make my lifestyle work.
When my income/assets went beyond "stable" and into "choices" we had to stare down our priorities.
One thing that occurred to me was whether I was setting up my kids for a life of contentment if I set their expectations (cars, clubs, etc.) such that they would need a top 5% income to support the lifestyle? Would they feel like failures if they were "only" top 10 percent and couldn't afford the lifestyle I could? Would they drive themselves into debt faking a higher lifestyle? One daughter wants to be a chef -- am I setting her up for misery if I train her that she needs to make big corporate bucks and belong to a country club so that she's not "going backwards?"
Though we could easily belong to the country club and my wife could buy a Mercedes, we decided that we wanted to establish life expectations for our kids that didn't box them into a consumption mindset.
As a result, we live hugely below our means. We live in a nice, but modest home in a stable community with good schools. Our kids have friends who are "rich" (lifestyle) and friends who live more modestly than we do. My kids earn their own spending money and are genuinely surprised if I pass them a $20 and tell them a movie with their friends is on me. (Actually, they usually turn the $20 down because they're proud they have their own money). Yes, they have iDevices but rarely new ones. Their first cars won't involve twine and bad brakes, but it will also not be the new cars some kids in the community get. (How can you ever feel good buying a used car if literally the first thing you drive is a brand new, $25k car? What does it take to give you that sense that "you made it"?). No Uggs in our house, they get Bear Paws for 1/2 the price. They know where everything is at Target. They're know beyond a doubt that we don't keep up with the Joneses and that's OK.
I relish taking them on big, life experience trips that we couldn't when I was young -- we've hiked in Yellowstone, swam under the Napali cliffs and watched the stars among the giant sequoias. When we do those things or splurge on something nice we talk A LOT about priorities, making choices to save for a vacation, etc. They know that we value shared experiences more than stuff and you have to know your priorities.
They will have it easier than I did, but they WILL NOT think you need a BMW and a country club membership to be a success. I want them to be no less contented and no less confident in their abilities than I am.
I don't have life figured out, but I would encourage you to invert your thinking for a minute:
Instead of thinking about what you want your kids to have, think about who you want them to be...and what consumption expectations they need to live up to in order to not feel like a failure? If one of your kids is a 40 year old teacher making $80k a year and driving an old Honda, will he/she feel content? Who's all the stuff really for?
You never really know how your kids turn out until they are adults, but as my daughter has gotten older she's started to figure out that we're comfortable. That said, when she came home and wanted to do a $3k exchange program, we told her she owed us $1k of it. She didn't flinch. Got a summer job and saved every $ from 1 to $1000. Didn't spent a cent on anything until it was paid...and she's really proud of it. She knows her priorities, she's confident in her ability to earn her own way. I hope she'll keep her priorities and be content.
My $0.02. Hope it's helpful.