Gonna be that person.
Where do these young girls end up going, and who is going to raise them? They clearly aren't able to support themselves. Yeah, they were scum yakuza before, but at least they were able to feed themselves.
If heroine is wise, she'll court the villainess. With the villainess taking the place of the flag characters twice, she is clearly the secret love interest character.
Merchant Guy seems like a genuinely good guy trying his best to fit into an ideological hierarchy forced upon him. He could be the happiest guy in this series if he just forgot about being "in charge".
It was great while it lasted. Finished on a good note of the male healer doing it because of his dream.
...That said, the english title of this series is truly terrible... Sexiled?