I just played this game for the first time and I share some of your speculations.
Does anyone else think the crone is princess' sister, and she tries to protect her ?
A few of us have speculated that. Welcome to the team.
If the days matter in this game then yes having money at the right moment should matter!
Also i'm done going back and forth i'm just gonna start over!
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I do think that!
As of right now, you can get exactly the same amount of money in exactly the same amount of time without allowing things to proceed between Evelyn and Thaddeus, assuming you wait to interrupt them until Day 6, which is the first time the walkthrough has you spy on them. After that, you just need to accelerate your pathfinding training with Erato. The only reason the walkthrough has you wait until Day 17 to complete the training is to have Perversity 4 before hand. You can do it earlier, but some options, such as
Ass to Mouth, will be locked although that isn't really important. You will have saved 2 dayparts by not spying on Evelyn and Thaddeus, and you can use those to Hunt Boar one extra time, earning 20 copper, which is exactly the amount you lose for interrupting them on Day 6. Assuming you're trying to accomplish the most in the shortest amount of time, which is one of the walkthrough's goals, you can find yourself on the afternoon of Day 22 having accomplished everything other than watching Thaddeus and Evelyn in the game. It just takes some forethought and rearranging of events.