Barring the dev self-insert/Kety thing which I don't like, but that's just a taste thing, there are two main things taking away from my enjoyment when playing the game.
First is having to constantly check on the events for the girls.
It would be nice with a UI element telling you when there is an event at the current time. Like when it's noon on a Friday it could say "You should go to the beach to see Nella." Or some similar version of their hint. Maybe an expandable element or something. It is just annoying to constantly go back and check where you have to find the girls. Since you have to progress with all of them, you have to remember the date, time, and location for the 12 different girls. Especially since you often have to sleep before the hint refreshes, and you never know when a new event might get unlocked so you basically have to check all of them every time.
Or maybe a calendar for the week or something so you can easily see the girls' schedules and where they are at. Either just the events or where they are on the map.
And second is the Love/Lust system.
It probably gets easier with more money later, but with the Love/Lust decaying over time, it just feels like a Sisyphean task to keep the Love/Lust up for the 12 girls, so I find it hard to bother. If the interactions were just designed to be seen once, I could understand it, but then I feel they should just be events. I can understand wanting to make money more relevant, but if you are meant to make the money from deliveries, the events with the girls already stop you from delivering a lot of the time, and if you are to do it from the casino, then it is actually just Sisyphean grind.
Sandbox games gives a lot more freedom and leeway for writing, but it is also harder to make well since you actually need some game design and it intrinsically takes away from the narrative and immersion(though with a comedy game like this, that isn't an issue). Some games do Sandbox to give freedom to the player, but since the story here is locked into Harem since you need to progress with one girl to progress with others, there are no real choices there, other than a slight change in the order of some events... I don't remember why I started a TED Talk, but my point is that besides a small feeling of freedom, the sandbox elements are currently more annoying than enjoyable, which is sad since I on the whole like the game.
Anyways, I was just a bit frustrated so I had to write something, but now I'm going to go back and finish the game(Well, the current version)