What if the Pegasus framing story was ANOTHER holodeck re-enactment? During the Titan era, Riker and Troi could be conducting it as part of a therapy session to work out lingering issues with Pressman, decide how he could have handled the situation better, etc. An additional simulation of TATV is just an incidental part of that. It'd explain the differences in their appearance, the lack of immediate relevance of TATV to the Pegasus incident, and the lack of sync to the Pegasus events. "I'm ready to go talk to Captain Picard" just means he's come to some new conclusion. The exercise is over.
I don't have much desire to rewatch TATV just to see if that would work. Anyone know if there are specific references in the episode that keep it from working?