I know that in V, he physically appeared and even before V, I had seen pictures of him online. However, before seeing the pictures, I mostly envisioned the III version and the San Andreas version, though LCS isn't too far behind, to look somewhat like radio host and former wrestling announcer Todd Pettengill for some reason. Other thought was maybe Michael Cole, who is also a wrestling announcer, or at least something similar. He gave me a nerdy vibe in III as well as in San Andreas.
As for Vice City and VCS, I thought a nerdy guy trying to look hip with either a mullet or long hair. I would have thought the concept art for the V-Rock album cover, but the VCS version probably would have tried the same image except a lot nerdier. Bear in mind, it was two years before VC, and I think he was supposed to be an intern or co-host and not totally up to speed with the images, hence Couzin Ed's verbal abuse to him.
As for IV, well listening to Integrity 2.0 made me think of how he described his looks in one of the segments. I can say that he might have had the image as shown in V, except I think in EfLC, I think he said that he had facial hair.
I know I should probably say about the other radio hosts, but seriously, some of the ones in San Andreas made me think of the people who voiced them. Like I thought of the Fourth Right MC looking like Chuck D or The Funktipus looking like George Clinton. You get the picture.
Overall, I am just wondering.