I agree, this achievement needs to be tweaked abit so it makes sense.
Honestly I haven't even tried to get the achievement since I've never cared enough about them to specifically do something to get one.
I agree entirely with the OP.
And when you compare life in our typical settlements to what's out there in the wasteland? Our settlers have food, security, a warm place to sleep and access to company, commerce, medicine and booze. They should be tap dancing in the streets.
Contact the United Nations. They might be able to convince Bethesda of the imperative nature of this. They would probably give a rat's ass that your benevolent leadership isn't being acknowledged.
...or just ignore the worthless achievement until it either gets fixed or you realize that spending hours getting worthless achievements may not be the best use of your limited time on Earth?
I was wondering why I could not get this. Its a bit buggy it seems.