Two times in fact, checking for as many possible paths I could.
The death of [REDACTED] seems unavoidable. To get the "best" possible ending, gotta NOT be possessive of Gloria, NOT go with the dubious things (pregnancy pills) Mio wants you to.
Jessica and Kaoru are happier staying friends (couldn't get a happy lovers ending, just a sad lovers ending for them).
It seems like you can screw around with the maids, but probably(?) can't be a dick to Rina (I can imagine her not saving you at the end if you are).
The humour is...interesting. Not for everyone, to put it mildly. Like are players supposed to respond positively to being called coomers or that you suck? Really immature and dickish narration, ngl.
All in all, it's ultimately the player's choice on how similiar you want to be to the player's dad, and the ending changes for the "better" the more you are different.