So, I have a bit of a theory to posit. It's about Dean.
But, something that might at least be entertaining to think about. It involves Dean being more than he appears to be, but a more positive spin on it versus the "Dean is secretly villain" theories I always see pop up.
Though, fair warning it's the definition of a crackpot theory so take none of this too seriously. Also, some story spoilers for various routes/paths/endings.
Simply put, Dean is from a rival family in opposition to Memphis' mafia. It's mentioned during his bad ending that he comes from a massive family of bears. What if that's a separate mafia family? David, knowing he's about to die calls in a favor to Dean's family. Mama bear agrees and after David's death, sends one of her sons to watch after Dave. He comes into Dave's life not long after David dies, in a way similar to a romance movie. What if that was planned? The reason he acts the way he does in the beginning of his route? He's simply playing the role of the Casanova he feels he's supposed to. Notice that the act drops around day 10 when he realizes just how fragile Dave's mental state is and that the flirty thing wasn't what Dave needed. This is also when he starts developing deeper feelings for Dave.
On Tyson and Orlando's route, he handles the date and breakup well. Realizing that Dave's feelings were elsewhere and maybe it's for the best in terms of Dave being happy. He's blindsided on the other three though, his mission is in jeopardy at that point and he'd started to have feelings for Dave.
Dean is far from the flirty, dumb, himbo people treat him as. He's smart, cunning, and capable with maybe the highest skillset in the group. He's calm under the stressful situations we've seen him in (path F and G) with C and D obviously lacking data. He's shown handling Oswin's revolver in the title art and chooses the close quarters fire axe as his weapon of choice in path F and G, so he can apparently fight. He never really directly involves himself in the group planning sessions, choosing to stay back and observe mainly. Look how often he's keeping watch over the group in the background. Think back to his behavior during some of the bad endings. In Roswell's, look how quickly he wants to get Dave away from that situation. The only ending he doesn't in some way stay with Dave is Roswell's (and his own of course) where Dave is under Tyson's care and they both leave the area, away from Memphis' influence.
For this, I'd include Dom as potentially being from the same "family", but undercover. The sheer fact a "Bad Ending: Dom" exists, means the guy has a good ending somehow.