I can share my personal experience, but it echos some of the things jaymar is saying.

I bought 3 years ago. It is a small home on a bigger than average lot around here. It was built in 1942 and isnt in the best school district. At the time, the opportunity was right for me to buy. I had the money and can afford the payments. Here is where the fun begins. A house that old needs maintenance, that equals to time and money. A lot that big needed constant gardening, that equals to time and money. A house that small is fine for myself, but it will not be the most ideal place for when a little b00gers comes. Being in a school district that isnt great will become a problem down the line. That and the home as lost value that it would not make sense for me to sell and take a loss.

In short, I wish I would have thought more longer term. Owning a home and only being able to own only one is a huge commitment that is going to tie you down to certain things.