Awesome game, definently my favorite released in the last few months.
1.I don't see a problem with the grind as your not limited by time or anything, there's easy ways to make money by just climbing up the mountain early game, late game you care even less.
2.The girl's get way more likable as you progress, at start they may seem kinda boring and very stereotypical but it gets better as they start to open up.
3. I may be biased cuz this is my kinda game (sandboxy dating sim/manager)
P.S. : To unlock the final ending you have to see all the individual endings first, saw some peoples in the thread asking about it.