In a 3 way race the Republican could possibly win, the Republican governor is very popular and she could have coattails BUT Chris Shays would try to save his own House seat by supporting Lieberman for Senate. In fact, he's already endorsed Lieberman.
As for West Virginia, it has gotten too conservative for Byrd, but he's an institution in that state and will probably occupy that seat until he dies. That's my take, until I see any polls on that one.
I think that Lieberman would win big in a 3-way race. If he runs as an independent, he might caucus with the Pubs if they give him a nice chairmanship. That would give us a net gain of CT.