I'm a life long Portlander and Blazer fan so I'm VERY familiar with Damian and the Blazers. He over-achieved out of college but does seem to have plateaued. He's obviously an amazing talent but does fall short in making people around him better. It's hard to say what his best fit would be. Being a ball dominant PG is tough unless you're REALLY good - Westbrook, etc. And even a guy like Westbrook is limited as far as winning titles.
Damian's a good to great shooter/scorer, a mediocre passer and a poor defender. So, where does that leave him? I'd say at the end of the day he's in the good not great category. The Blazers have endless problems with roster, desirability for free agents, management and other things. Damian isn't going to lead us to a title (or even a 2nd round playoff series) anytime soon but is certainly fun to watch. It's just so tough - he's 99.9% of the way to being a superstar but just doesn't have that last little bit to push him over the edge... not many players do.
Aside from any critique of his game, Damian is 1000% a great citizen and overall person. Qualities that are often lost with today's athletes.