@musicfreak12
The 1st on is the damn king. Dunno for the 2nd one, but it's the "I'm thankful that you're the reason she can smile now BUT DON'T EVER THINK OF DATING HER" daughter. Also the man who spread the hair treatment products to the noble side. Silk's introduction is on Ch.12 btw.
Eyyup, it's that jerkass king; the same annoying king that gives him the whole messed up area.
For the pirate princess(or duchess, I forgot) thingy, he actually just sent him to spread the pump and cholera treatment there as a 'good relation' sentiment, with his sick princess' marriage cancellation as the fair payment (AFAICR). Thanks to his luck though, he got embroiled in some royal fuckery there, and ended up getting him the actual recognition as someone who's capable enough as his daughter's groom... and the king's wariness of getting threatened by our MC's
rotten luckcapability.