Hey GrizzledOldGamer!
Thanks for taking the time to drop by and give your thoughts/feedback on AHITR, we greatly appreciate hearing what folks think about the game and areas that need improving.
I can give some context and info regarding the points you brought up!
In regards to point #1: Naomi's nipples. Originally this was a lore related reason. She had pink nipples due to her witch blood, but it has been brought up a bunch by players over the years/caused confusion that we ended up changing them over time, so this is why you'll see her pink nipples in earlier scenes.
Point #2: Navigation. The map will show whenever a girl is in a certain room, at that particular time of day and the quest log usually shows when/where you can proceed with a girl/when they come to you! In extremely rare cases we have some bugs with the continuity of where girls are, which have been fixed over time.
Point #3: Money. We do agree the money system isn't as good as it could be and we're looking into it down the road. Initially, money was used for going to the bar with Naomi, but as time went on
I hope this insight is helpful into the way some of the stuff is laid out in AHITR and again, much appreciate you taking the time to play the game and give us your feedback!