I would do it again. The debt is awful, yes. But compared to pretty much everything I did before med school, med school is great. I was not really awash in a multitude of lucrative options for my future. Most of the work I did previously was a near minimum wage grind, or pretty dangerous, sometimes both.
I loved the first two years. All I really did was set my own schedule and lie around and read all day. Granted, one doesn't really get to choose one's reading material in medical school, but it was all stuff I really am pretty interested in out of general curiosity anyway.
Third year is a little awkward, as one is constantly being evaluated in an environment where everyone knows a lot more about what is going on and how to do things than you do, but it still is not nearly as lame as many jobs can be. I kind of like reviewing what I have learned and taking multiple choice tests so studying for boards is actually kind of fun for me.
Your life does get kind of insular, and people you know may be out doing interesting things and amassing wealth or producing art or just having a really good time, while you slog day in day out in medical school. So there is that. But if you really involve yourself in your rotations, you do see and do some interesting things. Surgery in the middle of the night is exciting, as is L&D. Floridly psychotic patients make for some memorable experiences. Sometimes you have got to learn to enjoy where you are at, just for the sake of the experience.