In my second paragraph, I simply meant that by clarifying the relationships, the narrative becomes simpler, not only does he avoid anyone being a tenant, (actually, I guess Dana will be Willi and Miru's landlady now...), but he doesn't have to make a story that is plausible to both meanings. I mean, Dana and Gina have mentioned their brothers, Kat and Zoey have brothers we've seen, there's no problems understanding the dynamic - it's just their identity is clear. We know exactly what we expect of Stephan and Lucas, Ocean can focus instead on telling us why they're important in the story. In the same way, defining these relationships allows Ocean to set the conditions for the story and lead us directly, rather than keeping everything opaque.
Well, there are already other AVN's on Steam that have characters who have a sexual past, yet they're going to college for the first time, so it's certainly possible. In the old version or now, neither WiaB has had Willi do anything until Monica appeared. I guess Ocean just has to find a way to keep the past reveals minimal, especially as he cut Summer's kiss from SG.