Point being, I think people are more aware of the unattained wealth above them than the levels they've already surpassed. (Myself included). The comment you replied to strikes me in the same way, though not nearly as blatant!
Fast forward... I own a house in a rural area and have a family. I'll likely never have that cabin in the mountains, and I'll never be free of having to support my family. That's my fault though..I took the path of least resistance and ended up where I'm at - I didn't take the path towards what I dreamed about having as a kid.
Regardless, perhaps make it a goal to do this when you retire. It will give you something to work toward and possibly quell some of your regret.
If it's on your mind this much, and I'm no expert here, you might want to talk about it with a professional. You can't let this stuff bottle up and eat away at you from the inside.