Thank you. Is there any indicator on how to make these choices/progression?
I feel like the game forces you to stumble around against every single wall until you make a sliver of progress. It really lacks a hint/guide system if events are going to be tied to days and time and preconditions...
There's not an exact guide, but if you unlock the Patron only app on the phone (ideally by supporting the dev and getting the password along with each release, but there are other ways) then the hints for each Corruption Point give some information on how to achieve it.
For example, the Nerd's nighttime event that is unlocked by the sleepware is called "[Nerdname]'s Raid Companion", and the hint is:
"Visit [nerd.first_name]'s room on a Thursday night after getting ready for bed. Distract him from his [cog_title.name] raid by getting on your knees and under his desk."
So it should be clear what day and what time slot you can get the event.
Similarly for the Jock event: "Mom's Workout Distraction", the hint is:
"Pick up \"Brotein Powder\" for [jock.first_name] at the mall, then check in on his late night workouts on Tuesday nights. Help him burn off some energy."
I agree that a couple of the events are harder to work out the conditions, for example Slacker's "Saw a Sister's Boobs" event is tricky to arrange, but it's not impossible to work out if you treat it like the puzzle it is intended to be.
If you *don't* use the phone corruption points app, then it really would be stumbling in the dark... but I can't fault the dev for putting that thing in the patron-only zone. Because it is really only a trivial protection and parasites* leak the password microseconds after each release.
(* I say parasites because it's an accurate name for pirates who feed off the efforts of the dev and funding from the supporters, and then actively damage the Dev's income by revealing the secret. If you want developers to make games, you should support them however you can, not make it harder. If you genuinely can't afford it, then go ahead and copy the game, but don't reduce the dev's income potential).