Well,first of all,i aint using the logic we use on the usual way,i'm using the screwed up logic that permeates the peasant world,as it seems,he never was paid for his work,and without the cheat,he is handed to this shitty adventure with only some coins and a lot of ambitions,so i'm fucking impressed that he at least thought on paying them to tend the plantations(maybe his father treated just like that and he is simply repeating the behaviour).
Secondly,we tend to forget(thanks to the MC attitude) that this is a medieval world,and by nature racist and seclusive as fuck,Rosy even states that before the MC offer help,no one even bothered to do so for her being a Halfling.
And lastly,the MC behaves accordling to each family,but seeing that he is an adventurer,no one seems to care too much,as long as he returns alive.
As for halflings,the very existence of their kind is depicted as a homey and carefree people,they can be like us and have flaws,be jackasses or annoying pricks,but even with all of that,they still are the kind of guys that dont think twice before sharing a drink and some stories with you.