Portland should dump Hickson for whatever they can get for him.
He is not part of the long term solution there and he is about to become a vastly overpaid player this summer. Portland should cut ties with him as soon as possible for whatever assets they can pick up for him.
If Lillard/Wes/Batum/Aldridge is the core, what should they add?
Very thin beyond those four players. Is Meyers Leonard the franchise 5 going forward?
For Hickson? They are not going to get anything of serious value for him. A low first round pick. Something like that.
As for their core = Wes Matthews isn't a core player. The other three guys are core players. So they have a PG and two forwards in place. So, the Blazers are still looking for long term solutions at SG and C.
Meyers Leonard? Maybe. It's too early to say. Showing some promise but it's only promise at this stage. Even if he comes good, he is still a few years away from being what they need him to be.
From the way they pursued Hibbert in the summer, it looks like Portland's first priority is landing a center. I expect they'll continue to search for that player. Someone to anchor their defense alongside Aldridge.
I don't think they should be worried at all about their weak bench at this point. They need to get the core of their team sorted first. They are still at least one high level starter (maybe two) away from being where they need to be. Then they can worry about their depth.