First of all, i have to say that i trully like this kind of game, where you ( the main character ) is not a kind of saint example of virtue, like many classical games.

Also the Relation Sally-Rachel, is cute :O
Now i have sort of trouble with the game, the more i play the more i have the feeling that it's a western-RPG, stuck and struggling with J-RPG's mechanics.
I mean, like many western-RPG, fighting is not the main focus, it is present ,it is something you must know how it's done, but in the end it is just another tool, that allows you to advance in the story.
And in this way you did trully great job
You can have multiple job for earning coin, you can help or doom people, you can forgive or punish. Depending of the time of the day you can do action A or action B etc etc.
Even if your goal is clear in your mind the way to achieve it is totally up to you.
So in in this your game is a totally win for me
But regarding what i said about "struggling and fighting against an J-RPG mechanics " it's all about the fights and rewards .
I have found fighting very un-rewarding (if not a total punishement)

In a classical J-RPG the patterns is like this
" You win the fight, or you go back for farming level and gold "
And here is the deal :
- the only way to get exp is by "killing monster" .
- The way to make gold is everything except Killing Monster.
So if leveling up is out of question, then you go back to the jobs available and it take alot of time : the job itself (all animation involved ), and the travel and doing everything A lot of time,
=> because of course, you will not stuff only Rachel right ? 4 people in the crew >.<
And ofc, this means you did not lose your money in the Bar event c

( yes could fight him, but teehe => it's a fight, need gear and lvl

)
Many time in this game i have found myself like a zombie basically grinding/farming, but in a very unusual way @_@
I also think that you made the choice that monster doesn"t give gold, in order to push people into the job you created in order for them to discover your work and the effort you made in the animation.
SO, what i may suggest would be, huuum, some quest/event giving exp and or some "monster drop" that you could sell at the adventurer in the Bar or to another NPC created for this effect like :
" hey look, i have killed a monster around the city, thus making the area safer, gimme money now ! "
If by doing this you think it would bring too much income and resulting in the player taking the boat too soon and skipping all your work => why not adding an extra boss right after the player pay the fee ?
encouraging them to do farm just a bit more