AdorableRomaine I had a chance to play through chapter 2 and I liked it a lot. More antics, less cringe, well done. I appreciate the layout of the town, and it I like it better than just have Tamara telling us about her exploits in a static fashion.
I did have a thought on a possible way to improve the gameplay and assist in adding content in the future, but I can accept that it is probably not a priority. Feel free to ignore this suggestion, but I present it here as a thought on a way that you could proceed that you might not have considered, but that the "scenes around town" playstyle would be perfect for.
I think it would be cool to see scenes populate locations as other scenes are viewed. I.E. Before you meet a character, they only have their introduction scene available, but the scenes around town with that character are added once that first scene is viewed. Other progression options are sensible as well, like day 2 of the Ice Cream shop isn't listed as an option until after you have completed day 1. It wouldn't need to change existing content, although it might make it seem like the game has less content available if some scenes are hidden until prerequisites are met, but it would give the player a sense of completion and figuring out how to unlock scenes could add a progression element that is currently lacking. It could also force the player to backtrack to a previous location to see a new scene they unlocked
I'm pretty sure that as far as coding, if each scene has a boolean variable that gets checked off once it is viewed, and the menu options check for the appropriate boolean before showing the new scene in the list, I think that would cover it. (I don't code in Renpy though, so I may be over-simplifying what it would take.)
As an added benefit, there would be the possibility of having a scene that evolves over time based on player progression. As an example: There could be a scene added where Tamara could host a girl's night and invite all of her buddies out for some exhibitionist fun, and the content could change depending on which girls she has encountered at that point. Then a different girl's night out scene could represent more/different girls as she encounters more people.
As a final bonus, it would be easy add in a dialog box at the end of each update which says something like "You have seen all of the content for the current build..." and probably plugs your patreon and such.
Just an idea, and feel free to take it or leave it. Thanks, regardless.