Well first of all, it's not "I wish I had less space" but rather "I wish I had the goods and experiences I had to forego in order to obtain and hold onto this extra space".

But anyways you're missing the point. For instance my house had a 'dining room' when I bought it, but I made it into something that I use every day (music studio/band practice room).

The conventional part of me would have just kept it a dining room, and used it maybe once or twice.