I found that going and resting in the private rooms between handing in deliveries for those particular characters (and one other in the region I won’t name, but you will know when you find them) and they would send me an email that I’d then read and then the next deliveries would move it forward a little bit more. So just repeat that process a few times and it will move forward. Also, I believe the amount of likes received from any deliveries/lost cargo you send their way will be applied retroactively to the star levels when you get them past those thresholds, so don’t feel like you can’t drop off a bit more than you need between rests.
Hope that helps :)
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