I would think if he's going to follow a similar progression to the main game that as far as the lewd scenes go, you'll get Kira first, then Alice, then Lisa, and Anne would be last. Not sure what his plans are for Olivia and Kate. Olivia gives it up pretty much immediately if you're on that path but Kate takes awhile. With his own scenes added anything goes though.
I'd actually be surprised to see the porn movies so early unless this is going to be a really huge update. Doesn't Max normally go through most if not all of the erotic massage stuff with Alice and Anne first? That hasn't even started in the current version yet. The couch massage with Alice might count towards that at some point but currently just adds normal massage skill, not erotic. Not that I'd be complaining if it did end up in this next update