He won't end up with the Yanks (they said no to the prima donna treatment he wanted) and he won't end up with the Rangers (his ERA would surge and wins would be harder to come by). It's the Astros or the Red Sox. And he was able to watch Beckett, Schill, and Papelbon this week up close.
I think the odds of him joining the Sox should he decide to pitch again are probably 75%. The Sox have already announced they will be retiring his number at some time in the future. Roger has accepted that he will go into Cooperstown with a Sox cap on and he has embraced it. He is friends with Wake and coach Al Nipper and Pesky and several other Sox players who hang around the team or work for the team. And his wife (Debbie, I think) loves and misses Boston. She was upset they ever had to leave. Roger said the kids saw the video the Sox made and everything and seem to be perfectly open to the idea, too. JWH will pay for Roger's homecoming, for him to get a chance to right the wrongs of 1986-- to win a ring in Red and White, because it makes good business sense. He would not be the ace of the Sox. He'd be the #3 starter and have only the pressure to come here and be a team player and be Roger Clemens-- do his damndest every outing to win.
He wants to get 193 and be #1 all-time in Red Sox wins, ahead of some piker named Young or something. It makes sense for everybody for him to come back to Boston.