Hi BlueHouse,
I find your posts really interesting. I'm the same age as you, single, have similar income/spending patterns (though both are lower in my case), and my big expenditure is my wonderful house in a vibrant urban neighborhood, which I LOVE. I have a bit more in savings (just over $1M split evenly between retirement and taxable). I also have an investment condo, although mine makes a small profit ($5K last year after all expenses) and has a lot of equity, about $200K (terrible return on that money compared to what it would have done in the stock market, I know...)
I recently learned that my cushy six-figure job is going away in six weeks and it's forced me to re-evaluate a lot of things. I have the opportunity to take a similar job, which would allow me to maintain the status quo. I'm also thinking about doing some independent contracting, which MIGHT some day make close to what I can as an office worker, but probably not anytime soon.
One of the things I am musing about is the fact that, if I had never bought this house, and used that down payment to pay off the mortgage on my condo instead, I'd pretty much be FI now. I'd have saved a ton in the two years since I bought the house, so would have even more in savings, and my expenses would be low. This job loss wouldn't be so nerve-wracking, and I wouldn't feel the need to jump into another office job right away. I could pursue consulting with no fear. Or do nothing at all for awhile.
I could still do it by selling the big house and moving back into the condo. But I'm just not sure I want to go back to living in 900 square feet. And I have a child who adores this house, our neighborhood, his finished playroom etc. But I know these are all excuses: "we can't live without X!" Of course we could. I'm just not making that choice just yet. But I think about it all the time.
So I understand your struggles, and appreciate your perspective. By being here and embracing the concept of this site, you and I are different from many others in our position. We're not just overspending mindlessly. But we ARE overspending, and need to examine why we're prioritizing that over financial freedom. Good luck with all your decisions!