I don’t think whether a place is an actual place IRL or fictional makes a difference since the whole game is fiction.
IMO, it’s just IO reusing assets like Dexy Barrat, Heidi (whosit), Saito, Dexter, Portman, etc. 
I was thinking the hippie in WoT was different from the hippie that was in Landslide. But I could be wrong.
Edit: Nope. I was correct.
Now. As to whether or not there’s a pattern? I never really thought of that… And that kinda makes me replying to this a waste of time. 