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From what ive already read and with a bit of predictions:
This is a case like Eric.
Neither can be dated in the BASE game, but I'd assume that there will be some tales from Woodcrest about them. I'd also assume that this rule of thumb applies to Jay, Russel, Maxwell*, and possibly even Spencer**. Though, some are more likely than others. I assume that the list after the main character's routes are completed and the intro rework is finished would be revolving around the Main characters and interactions we don't see,(Logan and Eric's 'activity' at the strip club in Diego's route) or little "What if..?" scenes, like; "What if V, X, Y, and Z done this?" or "What if Adrian and Eric did that?"
Honestly, I have no idea whats in store for the tales from Woodcrest. Only time will tell.

*Maxwell is most likely not gonna be in a tale for a long while. He is a decently minor character, and i doubt that Xevvy and their team will release much about him.

**Spencer is a special case. If the character we're seeing him as is Adrian, then a lot of events will have to take place in order to 'Set the scene.' He would need to meet him in a different circumstance, like: What if Adrian ment Spencer before picking a route, or before the character(s) in the route are dating him? What if its like Tai's route, and the Main character and the love interest(s) break it off for a while? It's very hard to predict.