As for Tolwyn being captain of the Tiger's Claw... well, here's my theory:
He was captain of the 'Claw as of early-2654. On 2654.048 he was recalled to Earth to brief the Joint Chiefs for "several weeks" (Confed Handbook). That should take up the time up until around 2654.070 (~three weeks). He then headed back to the 'Claw, which was under refit at Sirius -- which takes us up to .072 (Red & Blue). Red and Blue happens, and Tolwyn finds out he's been reassigned -- and Captain Sansky is made commander of the Tiger's Claw. The WC movie takes place, Sansky is killed and Gerald 'unofficially' takes command (in Pilgrim Stars). Gerald expects to be formally made captain of the 'Claw (it's mentioned in PS that he never is), but instead is assigned elsewhere -- Captain Thorn is brought in to command the carrier. Some time passes, a couple of WC1 series' occur... and then we bring in an event mentioned in the Wing Commander 3 novel (referring to Tolwyn):
"At the height of the action he relieved old Captain Thorn, the ship's commanding officer, and filed charges against him for cowardice in the face of the enemy. Thorn had later been reinstated, but no one serving with the old man ever quite forgot the day."
Whatever event this is hasn't been told yet -- but it happened when Blair was a second lieutenant. The WCA episodes can immediately follow these, with Tolwyn still commanding the 'Claw. Tolwyn is then promoted to Rear Admiral and moved elsewhere just before SM1... Halcyon takes provisional command during Operation Thor's Hammer (Halcyon references commanding the 'Claw during SM1) -- and then Thorn returns when the 'Claw goes back to human space (in time for SM2).