After playing for a bit, a small guide I can put together is this.
There are several "jobs" you can do, most of which require certain stat points. Each "job" gives money and stat points (except school and tutor).
After working twice at a job, an h scene will become available (there are about 6 per job + ending). Doing an additional two after the repeatable h-scene becomes available unlocks an ending. Some endings give outfits. Each ending resets the 60 day counter and you keep all your stats.
Around the map there are many chests, each usually gives an item to increase exhibitionism or lascivious (or the chest will give 50k). You can buy outfits from two different stores in Kakafe town. These chests are your best way to level up the exhibitionism and lascivious stats early on, as collecting all will get you ~30 exhibitionism and ~50 lascivious.
I think after doing an ending a person in the bottom right area spawns that sells items to boost stats for 10k each. Similarly, above the house the dog will turn into a cat that trades stat points for money.
You cannot enter the nightclub, even if you did it's empty
The old man which you give a cocktail to requires that you get a blackbox from a painting inside the gray house you can lockpick. Giving him this box unlocks a shop which allows you to buy any outfit in the game, this is how you get the swimsuit, vest, and sportswear.
Most jobs have 2 ending slots in the gallery, including father and brother, which seem to be tied to the lascivious or exhibitionism stats
