Well, I'm currently working on the next story beats for Natalie and then I'll open up a poll on Patreon to see what people want me to focus on next. Basically, the goal is to have a storyline for each of the students and only some random stuff for the teachers and other NPCs, unless players really, really like them a lot.
And yeah, currently the analytics mainly show how far people are going so I can see if any part of the story is boring or maybe people get stuck before reaching it.
And as for updates, I'd say the updates are going be a bit more frequent. I've rendered 54 new pictures this week alone for Natalie's rituals and a few more for Olivia's swimsuit continuation. Granted, I probably can't render this many shots each week depending on work, but I'll try to do as much as I can as efficiently as possible without sacrificing the multiple choices, routes and freedom in the game. If I could do this as a day job, of course I could easily push smaller bi-weekly updates and monthly bigger updates, but yeah...
As it stands, I can't develop each girl's story in parallel unless I get another enthusiastic developer to write/code or render for me, but I doubt that. Who gets content first comes down to Patreon votes, analytics and just personal preference, so your experience will ultimately vary depending on who you're rooting for.