Yeah, I love the settlements part, but the management is meh...
My suggestion (probably just reiterations of what other people are saying).
1. Automatically name generic settlers:
No job = Settler 1, Settler 2, Settler 3 and so forth...
Farmer = Farmer 1, Farmer 2, Farmer 3 and so forth...
Guard = Guard 1, Guard 2, Guard 3 and so forth...
Provisioner? = Provisioner 1, 2 and so forth ... or settlement names for them?
Store people = name of the store they're at...
If you re-assign farmer 2 out of 3 to guard 1... he becomes guard 1 and farmer 3 instead becomes farmer 2...
...
2. An interface to assign preferred equipment to people. Either at the workshop or through a computer terminal? The inhabitants will try to "withdraw" a predefined set of equipment from the workshop automatically...
Either for a category like farmers, guards, store people and so forth... and possibly also for each individual.
...
3. Possibly even letting me reassign newly arrived settles to task straight from the interface in 2.
So I only have to set up equipment and outfits once. I can then easily recognize who is who.... and if I assign more people to a task or reassign them... they're gonna automatically equip themselves for it ...