How would you rate Roose Bolton as a strategist (politically/militarily/etc.) in comparison to others who can also be comprehensively analysed in those categories (Stannis/Robb/Tywin)?

Militarily, it’s hard to say because he spent so much of the war deliberately throwing fights to weaken his rivals and then to overthrow King Robb. We’ve never seen Roose in command of an army where he’s really trying to win and has to fight a straight-up battle. 

Politically, he’s pretty effective in the short-run, but he’s got this weird thing about long-term ramifications of his act. He’s climbed to the top of the slippery pole – he’s got Winterfell and the Wardenship and the Starks seem to be gone forever – but he’s not going to stay there.