I think Miller is a very bad fit in Portland (can't shoot). They shouldn't sign him.
Assuming Rudy stays and Webster is healthy this year, Portland will have some decent outside shooting (in addition to Roy). I have to admit, it wouldn't hurt if they got a better shooter at PG. Then again, they didn't have Webster at all last year and he's supposed to be a great 3 pt. shooter (if he can ever get healthy long enough to play). But overall, I don't think it's a bad fit at all, especially for the money and the years.