Hm, I've been thinking a past prince of a kingdom who either died as its hero or hero-king...So, he'd have this desire to see what came to be of his country.

A thousand years later, that may be many things...maybe it still exists, and he's now part of its myth/legend - yet, his current self wouldn't be recognized as such, of course. Or maybe it's gone and/or his memory entirely forgotten by his people (possibly because Regret's influence likely has a way of overriding the greateness of any mortal heroes even if they had been affiliated with her).

Either way, I can see Yddrog playing into the 'see what became of this land and how all you did for them is now meaningless?' revenge appeal. I don't *think* my character would be willing to entirely turn against them, but maybe he'd try to bargain that he manage this land in the dragon's stead/for him when it's all over. He's almost certain to eventually turn to Regret instead, but I can see him believing Ydrogg that things are like this because of her, and he'd have to realize that no matter how hard he works for the dragon, things will be always worse. Now, if he has this realizatio too late...who knows.