I'm not sure that it was EXACTLY 30 years, part of torturing is losing track of time or screwing with it in some way, so Dean may have no idea of how long it was, just what he either thinks or has been told it was. I don't think the exact 30 years is significant, other than one - it makes the torture seem horrible if it has been going on that long (as opposed to the 4 months 'up top') and two - they needed a number to use and 30 was nice and even and that leaves 10 years of guilt for Dean to wallow in.
That aside, I think he just reached the point where he just couldn't do it anymore, he gave up hope of rescue and he just couldn't bear Alistair in his face one more time. If Alistair came to him every day, and asked the same question, that quite possibly might be worse than the torture: to be free, to not have to face something just that one more time. How many times have you gone into work, faced the same thing day in and day out and one day, you call in sick: you're not physically sick, you are just mentally and emotionally tired and just want a break. Of course in Dean's case, things are much much worse, but same principle. He just finally cracked.
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That aside, I think he just reached the point where he just couldn't do it anymore, he gave up hope of rescue and he just couldn't bear Alistair in his face one more time. If Alistair came to him every day, and asked the same question, that quite possibly might be worse than the torture: to be free, to not have to face something just that one more time. How many times have you gone into work, faced the same thing day in and day out and one day, you call in sick: you're not physically sick, you are just mentally and emotionally tired and just want a break. Of course in Dean's case, things are much much worse, but same principle. He just finally cracked.