I make more than my dad did at this age (he was white collar). My mom was a doctor's receptionist before I was born, then SAHM until I was in 7th grade, when she went back to work in the same doctor's office to help pay for my and my brother's Catholic school tuition (I was in the publics until the end of 7th grade).
The cost of housing is the true difference. My parents bought a small lot in a middle-class suburb of Detroit in 1965, the same year they were married. They rented a two-bedroom townhouse (rent was $95/month when they moved out) while they saved up enough money to build a small 3 BR 1 BA brick house on that lot. They moved into the house in the fall of 1968 - the house cost just under $16K to build. In the early 70s, they added a detached garage for $3K. Their house payment, in the last few years before it was paid off in 1998, was $300/month! $200 of that was taxes and insurance!
I got out of suburban Detroit in early 1996 because I wanted to get away from the auto industry and its influence (for worse) on Michigan's economy. I'm in Chicago and will make about $44K this year. There's no way I could afford a house or a condo here without living in the very far out burbs. On my end of town (NW side of Chicago), decent apartments are affordable. Like New York, there are many people here who are life-long renters, so unlike where I'm from, renting for years on end doesn't carry a stigma.
I just looked at the online classifieds for my hometown, and a similar apartment to mine looks to be about $100/month cheaper or a little less. Houses like I love (1920s bungalows/cottages) are $75K-$100K cheaper. But then the economy in suburban Detroit is in much worse shape than that in Chicagoland.
I'm in the first on my dad's family to get a college education, let alone attend. If I didn't have my degree and 14+ years experience in my industry, I would be making less. I'm also one generation from relatives being on welfare. My mom was born in 1942, the youngest of 17 (including two stillbirths). Her father took off in mid-1943 and was never seen again. Back then, welfare was primarily for women whose husbands had abandoned them or whose husbands were disabled. Her family was on welfare. They lived in the projects, back when the projects were for poor folks of all backgrounds, not for primarily black folks as they later became. There was a hole in the bathtub area. My mom's mom died a year after she graduated from high school, and she then went to live with an older married sister for three years until she got married.
My dad's family was working class and still is. I'm told my younger, less-educated cousins consider my lack of a mortgage a sign of immaturity (!)
but I also don't have a huge debt load on a relatively unstable income due to auto industry influence. I'm told they're all up to their eyeballs in debt.
You used to be able to get good jobs without having a college degree, but that's mostly gone. My mom retired in the late 90s (due to some health issues and change of doctors where she worked) and she was only making $10.50/hour! They're lucky my dad has a good pension from his 30+ years at Ford. Since I'm still single, I'm socking away 10% in my 401K. I'm not counting on getting married, although I really hope it happens (I'm 38). As soon as my car is paid off next year (only owe $4400 left), I'm going to really bump up the retirement to 15% as well as put other money away.
ETA: My parents had their own house at 26-27. I'm 38. They did pay for my college (I kicked in a lot for living expenses). But I'm much more careful with money than they were. My mom always liked to eat out a lot or cooked convenience foods. I get the impression from her comments that cooking from scratch is for poor people.
ETA2: I voted "same," too.