I obviously haven't play chapter 2 that long. Never.
You've never taken an hour to do Chapter 2? I doubt that I have ever done it that fast.
Actually, I have never really paid attention to the cooldown timers. But, it's possible that I normally get to the appropriate triggers at least once after they have run. It's worth noting that the countdown usually starts when the NPC is created, not when he finishes talking to the PC. In other words, the 15 minute countdown starts when Solomon is first created inside the Green Griffon Inn, not when he finishes chatting with the PC and trying to give him the ring.
I think the only time I have really broken that plot line is when I used the Recall Stone often (usually, I rarely use it). Between the Stone and not staying on the roads in the outdoor areas, it may be possible to avoid some of the triggers. And, once I ran away from Solomon in the Green Griffon and let him chase me into the barn outside before going invisible and using the Stone to port out. '>