So should I still be relying on the opportunities for hints on how to progress? They don't seem to provide too much information on what I should doing differently than what I already have been trying to progress any of the ones I have that aren't marked as completed.
I usually do give her money for bills, just haven't recently in the save file since I have been cycling through days quick trying different things to try and trigger anything new.
Is this something way down the line or what I should be trying to trigger next to progress?
You are in v.11 content and event is in 0.22. Lots of main story events to do before you get new events with Vicky.
Your Ann is not going to work in the evening and does not offer any lessons for Lisa. So your changing roles opportunity is not finished or story with Lisa has not advanced far enough. You can't get events with Lisa on Alice's stream as you never advanced Blog opportunity far enough.
Your blog opportunity progress is way back. Watch Alice on website, undress her completely and use extra dialog option, which allows to leave early and go somewhere else. You should have done that earlier. No idea if delaying Blog for that long did not mess up with changing roles and story progress overall.
You are still in original game content and guides for it are on other forum thread.
EDIT: it took about two ingame weeks to advance Blog content that you ignored. After event with Alice inviting Lisa to a stream, Lisa will start working on her lessons with Ann and it is the grindiest part of original game. I won't bother advancing your save further to check if progress is not broken.
