On another site the question was recently put to me:
What about a person who didn't buy a house 30-40 years ago when prices were cheaper and not has to pay nearly a mortgage payment itself to rent a small apartment or just a room in someone else's house? How can they even think about retiring or just slowing down work in their senior years?
My answer was simple: It was a missed opportunity they now have to live with.
Presuming the person did in fact have the means to buy a house 30-40 years ago (sure prices were lower back then but so were salaries) and didn't pull the trigger for whatever reason, it's a lost opportunity.
Life is full of these.
I should have bought Amazon.com stock at $14/share and Wal-Mart stock at $19/share but didn't (my wife still reminds me of that!).
I should have gone on to post-graduate school for a PhD but really didn't interest me much at the time.
I should have take a certain job opportunity some years ago but didn't and that decision lead to 4 years of pure Hell!
The wreckage of decisions and choice litter the sides of the road of life. Nothing we can do about it living a linear existence. And even if we could go back and make different decisions, sure it would have changed our lives and possible solved certain problems, but a whole new set of never-imagine problems may have arisen to take the place of the old problems.
With regard to the hypothetical person in the question above, at the risk of sounding cold, I don't see anything that can be done for them. Nor should it. They made their decision long ago for whatever reason. Holding out hope that somehow, someway in their later years a miracle will happen and they can now afford to buy (and operate!) a house is unrealistic, unless they win the lottery.
Home ownership may be the American dream but it isn't a given right that everyone will own a house. It's the attempt to have made the dream a right that lead straight to the real estate bubble and crash and the resulting historic record number of foreclosures we are still seeing today (as of writing this anyway).
Whether you accept Chaos Theory or The Butterfly Effect or some other life guidance philosophy, the decisions you make or not make today can have major repercussions on your life in years to come.
A journey of a thousand miles starts with but a single step.
Tread gently for it is my dreams you are walking on.