okay hold on I gotta express my autism too because I'm also hyperfixated on these games and have thought about this for a while! And also I care! I think it's nice to speculate on this sort of thing and it's really fun! No need to self deprecate like that, I love putting things together and linking all these pieces of a world so let me add on to this. Spooky Soirée depicts Periwinkle before he met Pastille but after Kamilla and Eleni met so it most likely slots in after Contract Demon but right before Starry Flowers. Also, Vinegar says she's 16 in Astra's Garden, but in the comic profiles her age is listed as 20. Assuming that the APoC profiles are more or less the same as the real characters despite being only sometimes canon it means that Astra's Garden takes place around 4 years before SATUS. In Charm Studies, Cassia says she's 17, and by a little after Starry Flowers, she's 23. That means that Charm Studies was six years before current canon making it the oldest game in the timeline. So, the full timeline is probably something like:
Her Tears Were My Light --> Charm Studies --2yrs--> Astra's Garden --4yrs--> Syrup And The Ultimate Sweet, LWT ch.1 --> LWT ch.2 --> Contract Demon --> LWT ch.3 --> LWT ch.4, Kaima --> Spooky Soirée --> LWT ch.5 --> LWT ch.6 --> Drowning, drowning --> Starry Flowers --> SF:MC, SF: TD (because, i mean, they can't really take place anywhere else).
Anyway, thanks! let me know what you think or if you have any additions, this was fun! :) Sorry I don't have LWT ch.7 or 8 yet, I'm still getting around to those