You have the exact same challenges. He just was able to overcome them better than you, by having/picking/convincing a wife who takes care of the home. You all made your choices.
I guess so. I mean, he's from a generation when most women didn't work and I'm from a generation when most women do work. He bought his house long before prices skyrocketed, I wasn't in the workforce until long after they did. So, I'm not sure it's a fair comparison, but you're not wrong either.
So your wife has to work because your house was so expensive? I wonder about the place where you live. When your boss bought his home, was it cheap everywhere, or did he pick an affordable location that now has become expensive?
It's not a must that woman work in this day and age.