I'm at this point in my life too. As much as I'd like to have a stable job and everything, there is that side of me that doesn't want to end up working in a cubicle for the rest of my life. Music is what I love, and I'm seriously considering Berklee. Corinpills brings up a good point, though. There is the possibility of being right where I started after Berklee, except x years later and x dollars poorer.
On the other hand, performance is not all they offer at Berklee. It seems like the way this thread is going, we're focusing on the risks of being a performing musician, not say someone with a degree in production and engineering or music business.
Now, I may be mistaken, but I would think that with training in those fields, I would be able to make a good living for myself. This is what appeals to me the most about Berklee: having working knowledge of something other than my instrument when I leave, and having a skillset that will get me a steady job rather than just being really good at playing wedding gigs.