Jester is an interesting place. On the plus side, it is right in the middle of things, handy dining, close to the stadium, right across the street from both Gregory Gym and the library. The rooms aren't bad, definitely a place to meet people.
On the minus side, it is huge, over 3000 students live there. It tends to be party central. My son has also applied for honors housing, but put Jester as his second choice. Many posters here will give you info on some of the smaller dorms and tell you to stay away from Jester, but they did not appeal to my son.
Do a search "dorms". There was a really long thread with lots of good info on UT dorms not too long ago. See if you can pull it up. It may answer some of your questions.
You can also change your dorm preferences for a couple of months online, so he can send in what he thinks he wants now, and change it later if he changes his mind.