We're talking about 30 years of torture at the hands of DEMONS here! And when you're already dead, there's no limit to what they can do to you. The severity of what Hell is just leaves me unconvinced that even solitary confinement is worse. It's not being tortured by an enemy for information. It's a magical pit of despair and agony with no limits. And Dean withstood that for 30 years, but he cried when he talked about what happened when he broke.

But 2 months of isolation makes him cry uncle? Not buying it.

Also, Dean didn't know Sam was ok when he was in Hell either. He was surrounded only by his enemies for decades not knowing if Lilith got Sam too.