Finished the game. It's an ok game that plays exactly like a VN with unnecessary movement.
In the gambling part, there are 4 opponents but only two of them are really "games" where you need to think (one is a puzzle so that kinda sucks if you try MTLing). The other two games are just decided on one choice, where you say "I can win this!" or "I can't win"
The scenes are recycled between the 4 characters but are animated.
The bad endings are really only if you lose multiple times to the same person. AFAIK, once you pay off your debt, it goes to a happy end, regardless of what happened to the girl.
+1 for a translation but I think there are more interesting NTR games out there.