I think he's happy with the situation at Liverpool. He's actually got all his top players after a successful season, not often the situation in Dortmund. He's always preferred developing players that has shown loyalty and heart, instead of buying upgrades - unless there is a significant upgrade or an appearent gap to fill.
He's a football romantic, and he's not a fan of certain aspects of modern football - success by splashing cash especially. And he'll whine about it, and dish out digs, whenever he can. The problem now is that is somewhat part of it, weather he likes it or not. I understand why people call out double standards and all that (especially after last year's spending), but I see the same Jürgen that was at Dortmund - saying the same things and trying to do the same things.
I wouldn't be surprised if he withdraws from top football after Liverpool. I just think top football is developing in a way that he finds hard to come to terms with.