There are some things Dame+CJ do very well. But perform well in the Playoffs together is not one of them. So yes, for some time I have been an advocate of getting someone to go with Dame who is a better fit all around for the team while they might not be as good of a one-on-one scorer. Also, they are fighting against a historical hill. In the history of the NBA, I can't find 2 ball dominant, smallish guards who don't play defense very well that have had much success. The closest to me is Curry/Ellis and while that was a fun, exciting, scoring duo, they accomplished nothing in the post-season.
Thomas/Dumars is also close in size but Dumars was an All-NBA defender which is something neither Dame or CJ come close to.
I like them both individually both as people and as players, but as a duo, it creates some gaping holes and I also believe, keeps the team from developing a rhythm at times. I would love to be proven wrong, but since CJ became the starting PG, the Blazers are 5-14 in the Playoffs. For as much as they are paid and the percentage of shots they take and the style they play with, that just doesn't seem to be a recipe for success. Yes they need better pieces around them but no matter who is around them, they are still taking a majority of the shots in an often efficient manner.
It's been 4 years. The sample size for me is over.