1. No, nothing different happens each time. Except: each ten times he solves the escape room and successfully escapes, confetti falls from the ceiling. The tenth time, it's just a little confetti. The twentieth a bit more. The hundredth time, it's so much confetti! It's everywhere!

2. Sure, he can experience those memories. He can't regain them, since he won't have those memories somewhere in his brain, but he can definitely see them in this event and get the Vibe that they're his.