Harbor Village reads
After the next Action you play this turn, if it gave you +$, +$1.
In both turns 9 and 12, you played a Hideout in between Harbor Village and Clerk. Hideout didn't give you +$, so Harbor Village didn't either.
Note that since you already had played the Harbor Village and had 2 Actions afterwards, you could have immediately played the Clerk in both cases, gotten the additional +$1 from Harbor Village, then continued with the Hideout. So switching the order of those 2 cards would have given you the +$1 from Harbor Village.