Good Question - tough to answer
I was brought up that if you can't pay for it (cash) you shouldn't own it. However, my parents are 67 and things were a lot different back then. My father paid $40,000 for his current house and with a few additions and continual updates is't worth well over $250,000. He was able to purchase new vehicles for $5,500. In fact, hew would make enough money, but a new car, quite his job and go fishing in Canada until hes was broke. He would then come home and do it again. Now pricies have gone up and the paybase hasn't imho.
Fast forward to me - I'm 29, graduated college and just bought my first house. I was lucky in that I was able to pay cash for college. Granted I think my insides are pickled from all the Ramen noodles but oh well. I got engaed to my wife and was able to pay off her student loans. When that was done I bought my first new vehicle (Toyota Tundra 2004 and still driving). Nothing fancy - crank windows, V6, not extended cab - and paid it off in 2 years. We had a small wedding that really didn't set us back. Bought my wife a Rav4 - had to finance it and probably will run the loan out - 4 years. She went back to school for her masters and we took out a loan. Also financed the house.
I don't think that's to bad for debt as we don't have any credit card debt and buy things only as we need them.
Now am I jealous of other people who have new and nicer things - yes. But then I think of the payments. My sled goes forward and may be a little slower (its a 1990 Indy) and my boat is ugly and rattles and would probably be worth more in aluminum then what I have into it. But both don't cost me a dime until I break something.
With the state of the economy, I can't see financing a boat, sleds, cars, house, student loans, furniture like a lot of my friends/peers. But it is a personal choice.
Could I be happier with more toys - probably. But I can sleep at night knowing that for the most part I can walk away.