No I don't see Bayless as too valuable to include in a deal. There are two lines of thinking about Bayless. Either you are so in love with him that you can't see the flaws in his game, or you believe he is a 2 guard trapped in a point guards body.
There are some in Portland who tend to be so in love with our players that they tend to overvalue them. Our general manager Kevin Pritchard has been accused of this by some. And it may be partially true. If so, it might explain why he has been unable to make a trade this summer, and at the trade deadline when he had that huge expiring contract of Raef LaFrentz.
As far as Kirk Hinrich, Portland fans again seem to be split in to two groups. Those who feel he would be the perfect addition to Portland and an upgrade over Steve Blake, and those who think he is more expensive and not that much better than Blake.
I tend to lean towards the latter one. I'm not convinced Kirk is that much better than Blake. He is probably a bit better as a defender though. I'm not convinced he would be a better shooter or distributor though. Blake is decent enough at penetrating, but when he does he is predictable and almost always kicks the ball outside. He isn't good at slashing to the basket and finishing, or at getting the ball inside. And when you have Greg Oden and LaMarcus Aldridge down low on the block that is essential.
Discussion on Blazers trading for Hinrich at Club Blazers