First I'd like to say first post and thread :D
Okay now to the topic, was I the only one expecting this. Okay imagine you being one of the characters during 400 days, and then you spot someone from season 1. Let's say for example you're Vince, and you see Kenny enter his car. Telltale then proceeds to give you the option to walk up to the car to talk to Kenny, but instead Kenny drives off as soon as you click that option.
Basically this would fall under the Dramatic Irony trope, where you know more then the person you're playing as. For example if Lily were to return in season 2, we'd know what she did in the past, but our characters wouldn't. Back to my examples, what if one of the characters were extremely close to the motel, and we know that's where the season 1 cast is hiding out, but our characters just keep on walking.
Yeah I know pointless topic, but this would have been extremely cruel for them to do so. For our characters to be near the season 1 cast, near Clementine and Lee, but only for our characters to keep on walking.