Re: OK, so
I think you should go for the PhD and see where that leads you, you're not making the ultimate 40-year choice. In fact, you can leave after a few months if it's not what you want. And you don't owe anybody or anything, so take the opportunity and if it's not what you want, fly away.
I will say that the depression thing could be very bad. Probably the money you have made playing poker will help stave off some of the standard gradstudent-type depression, however, U-Chicago is absolutely the single most depressing college environment in this country and probably anywhere. I have several friends who attended various graduate programs there and the place creates its own cycle of depression. If you are prone to serious bouts, this may be an environment you want to avoid.
-Michael
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