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Currently this just impacts the ending.

No. Paying once should be sufficient.

The path choices might need to be a bit more clearly one way or another, I think I may have locked Anna into the pure path despite my best effort to make her a turboslut town shagger.

Tower defense game needs more starting gold and/or wave rebalancing. The towers need better targeting priority, they love ignoring a near-death enemy to focus on an uninjured one which often results in scenarios where the easy kill gets away, maximizing loss.

Always a hard lesson when it first comes up, that being a dick is only really funny to one's self.

Going to need to invite Phoenix to the studio some day. To create fitness content.

Sounds like you've chosen a dialogue option that makes her hate you. I don't know if there's a way to repair a damaged relationship.

Being able to do the sharing routes for Anna and Samantha instead of having to choose one or the other would be cool. 

Especially if it means getting to share both at the same time later.