What do you think about this thought: since I'm taking the Doctor from pre-Time Lord Victorious (I always like to leave this as a possible option in RP games. I've only managed to do it once and it was beautiful.), maybe he does become TLV at one point in the future? I'd figure his massive attempt at trying to escape fails big time.
And yes, I'm pretty sure after 20 years the Doctor is going to break down at some point and let Jack in. Interpret that as you'd like (LOL) ;)