I don't see Felton being a great fit for Portland.
Hinrich maybe, but he's a big risk. He's been in a slump all season long and he has a big contract attached to him. If he could return to his old form, he'd be a decent fit next to Roy... But I've never been a fan of his ability to pick up fouls like a bigman.
Calderon is an interesting idea, but I don't expect us to make a serious run at him. I mean, as good as he's played this year, I don't really feel that he's a big enough upgrade over Blake to justify what we'd have to pay him this summer.
I'm a big fan of Granger. I'd love to bring him in, but I don't see the Pacers being interested in dealing him. I expect they'll want to build around him and Dunleavy.
I also really like Deng, but I don't see anyway the Blazers can get him without overpaying. If the Bulls move him, they'll want a bigman in return.
As for Portland being "scared" to move some of their players, Kevin Pritchard has never shown to be the type of GM who's afraid to make a trade. I really don't see the Blazers moving Outlaw unless is a no-brainer deal. It'd have to be something really special for Portland to consider it, because Outlaw really means a lot to this team right now. The rest of the pieces that you listed (Webster, Jack, Sergio, Frye, and/or our 1st rounder) all have potential for being moved in a deal to bring in a player we need.