I agree with the general principle that it isn't fair to say that Chris must me miserable because x and y have happened to him, and most of us would be devastated by that.
But do Chris' aspirations make him happier? In some ways they do, because he can live in a pleasant fantasy about the future. In other ways, he seems to constantly feel screwed by not getting it. Then again, he just keeps on dreaming, so it keeps working. It certainly makes him a much more mercurial character than he would be if he had a more realistic view of the world and his role in it.
As to Cole's happiness, do we really know how much his lack of success bothers him? I am sure he wishes his reviews were more respected, but does it gnaw at his psyche, or can he shrug it off and enjoy the nicer parts of his life?
Overall, it is really difficult to compare "happiness" across people. Our only reference points are other emotions we have had, not the emotions other people have had. I don't know if there is really anything meaningful we can say about whether Chris is "happier" than Cole.
That's my guess. I doubt Chris would have an attachment to much of the hoard, but cleaning it up is a monumental task that would be daunting for anyone to tackle on their own and expensive to outsource.
He may pick at it and list a few things. I could also see him trying something ridiculous like posting an ad for $100,000 for a house full of treasures..