I think it's completely normal to be in some kind of debt. There's going to be some point in your life where you can't exactly pay for something up front. When you go into debt, there is that initial realization that you have to pay them that $25,000 for that car and that it's technically not yours, but it's still normal. Eventually, you'll own that car. Eventually, (well, if you stay long enough) you'll own that house. You're not really throwing money down in a hole, you're just paying for something over time.

Really, if he's living in an apartment, he's the one living more constrained, isn't he? In 30 years, you'll own that house. He will be paying for an apartment until he dies. Sure, it's harder to just up and leave a house, but it's not impossible. If you are a person that wants to move around, apartments are great, because you can often be out by the end of the month. However, if you pay off a house, you now just have a safe base to work with. You can go live other places for a while, but if anything happens you have a free place to stay. If your conscientious about being tied down, then you shouldn't really base your life around where you live. Get an apartment if you want to move a lot. If you want security for life, get a house and still visit other places; you'll have something to eventually settle down in.