To properly act out an AOL-Bear there are a few things you would have to ensure.
#1 The AOL-Bear would have the oldest commlink ever made, whatever that was, he'd have it, and not even consider upgrading no matter the benefits. If he even understood the benefits or knew of their existence.
#2 AOL-Bear never checks his messages with his commlink. He goes into VR, goes to a host, and asks the host to show him his messages. He does this every time, even just to check to see if he has messages at all.
#3 AOL-Bear somehow only ever ends up in the worst chat rooms. The ones that are all matrix trolls, and one guy posing as a woman. The AOL-Bear will send the "woman" money for literally any reason provided.
#4 The concept of the matrix is not graspable by the AOL-Bear, he uses it, but has no concept of what it is. Essentially he thinks his "walkie-talkie" is pretty advanced to be able to let him fly around like a video game. Sometimes he'll hold down the transmit button as a kind of "lala i can't hear you" button for whoever he is talking to.
#5 The ring-tone on his commlink is actual audio of an old physical phone from the 1980's. He says if he sets it to anything else, he forgets it's a phone call and just stands there kind of dancing to the weird sounds coming out of it.