It really depends on the group of people you rock with...seriously. It can be as boring or as exciting as you want to make it. The rowdier the group, the more expectations start aligning with realty. Our advice is to find a cool group of people that can make the trip what you have built up in your head.
I've been to TTR before - but before Jamie and I met. Last year we went to a really nice resort in Riviera Maya. The 24 hour bar there would have families with kids of all ages hanging out all night though. Large groups of teens and preteens would be in the bar playing pool and video games at 2 and 3 am. Kind of a buzz kill. That won't happen at TTR. There will be plenty of surprises because no two weeks have the same crowd - the dynamics really depend on the people there at the time. If you go there to have a good time...you will succeed. And we will be there with you to make sure of it!