I know we never see the full picture, grass is always greener, etc. But I don't think this is uncommon.
Thinking of friends we see quite often in another part of the country, and like a lot and have known for years. Their 2 girls are about the same age as our DD & DS and we always enjoy visiting. But we always come away with the feeling that (as DW's mother says) "if they fell in a bucket of muck they'd come up smelling of roses."
They seem to have lurched with no game-plan from one set of fortuitous circumstances to another for about 15 years, without the wheels having come off the wagon yet.
They live in a lovely rural part of a very nice city - we are talking "stockbrokerish" prices. One of them is an academic and the other freelances, so how the hell they afford it I just don't know!! I know they bought their house at a good time, but then again so did a lot of people. And they've never had to venture more than a mile from their front door for work - it just seems to be that kind of place. No getting up at 6am to defrost the car, or travelling to a horrible place for work, or living in one for a couple of years.
It seems to be the kind of place where everyone knows everyone and does favours all the time. And they got their DDs into the local school with no trouble, even though some neighbours didn't.
It's odd - I can't decide what this feeling is. It's not envy exactly, as our life is fine. But maybe there is a whole story there and a whole load of suffering they haven't told us about? Or maybe some people are just really lucky?...
I'm going to get flamed now for saying people should have to endure a bit of annoyance to have a decent life. Aren't I? Go on, go on.