After a week of play, and some initial confusion and frustration with the Settler assignment system, particularly Provisioners, this system has helped me keep track of who's doing what, so I thought I'd share. I've read of others doing similar things, hopefully Bethesda will streamline this for us. Granted, this is more likely to appeal to roleplayers, ymmv.
My character build is focused on Intelligence, Charisma and crafting in general. Starting SPECIAL stats were:
Str: 3
Perception: 4
Endurance: 3
Charisma: 6
Intelligence: 8
Agility: 2
Luck: 2
Again, ymmv; I bumped INT to 9, then CHA to 9 as well, after which I grabbed any crafting related perks, as well as both levels of Local Leader. You can easily mix in upgrades to Locksmith and Hacker as well, or even go melee with a Str boost.
Settlers:
Use clothing to distinguish their different tasks, which I divide thusly:
Farmers - Anything with Jeans, Bandanna or cap
Guards - Raider armor, Sack Hood with Straps/Tubes, rifle
Scavengers - Scavenger suit, goggles
Merchants - Surveyor suit, Trilby hat
Provisioners - Leather armor, assault mask, rifle
(Everyone has a pistol)
Each of these looks are easiy distinguishable, and the gear is easy to find. As .38 ammo seems relatively plentiful, all settler weapons are .38 compatible. Merchants are only assigned to my "hub" settlements, currently Sanctuary, The Castle, and Taffington Boathouse, and Provisioners primarily come from these 3, which are all linked, as well as from a couple of outlying settlements. Basic settlement labor assignment is 2 farmers/2 guards/1 scavenger per 5 pop, with a Provisioner as needed, adjusted to focus settlements over 10 pop on either food or scavenging.
As noted, this isn't original, many others are using similar systems, at least as far as the clothing goes, and likely the division of labor.
But, a couple of things still bothered me:
1. I wanted to be able to distinguish one settler from another, beyond their basic assigned job; this was primarily RP based, but is also useful if you have multi-crop farms, as well as just for snout counting.
2. Provisioners....it's aggravating enough that you can't tell which route a Provisioner is traveling at a glance, but that frustration is compounded by not being sure where the point of origin is; Sure, I should remember who I assigned where, maybe I should have written it down, but...I didn't. You "can" figure it out by a lot of trial and error, and liberal use of the "wait" feature, but that's just crazy, plus not my idea of fun.
So, what I do is:
1. Name all Settlers. IMO, this should have been a feature from the get-go, even if it was as simple as tagging settlers assigned to farming with "farmer", as Provisioners are treated. Since that feature isn't available, my solution is to issue each Settler within a particular community a pistol, the one absolute common item, renamed for their job, and settlement. Easily done via the Weapon crafting table.
Example: I assign a Settler to farm in County Crossing, and dress him according to my specs for a famer. I also issue him a pistol I've renamed; he is now "Farmer Bob CC". Granted, I have to check his gear to see his name, but I can tell he's a farmer at a glance by his uniform, his name primarily tells me how many farmers I have at that location. I use an alphabetic progression, and throw in some friends and such for my naming, but you could easily just assign them numbers.
2. Provisioners. Easy to identify, thanks to the honking big druffalo, but incredibly frustrating to manage. What works for me, though not ideal, is to name my Provisioner's pistols similarly to the settlers. This has helped a lot with regards to expanding, much easier to see who should be re-assigned.
Example: I assign a Settler to run the route from Sanctuary Hills to Oberland Station. Dress and gear him accordingly. His pistol is renamed "Pro Bob Sanc/OS". Now, by clicking Trade with him, I can tell where he's going, and where he's from. If he was going from Oberland Station to Sanctuary Hills, he'd be Pro Bob OS/Sanc.
3. Merchants: Named according to their stall.
Example: Chems CC(chem merchant in County Crossing)
4. Guards: Named according to their compass position. I also tend to assign idle companions and named npcs to guard duty at my hubs.
5. Scavengers: Named for famous adventurers and scalliwags, fictional and historical.
Spent a couple of hours doing the running back and forth it took to get this set up, but now that it's done, it's super easy to reassign extra settlers, ringing the bell to gather folks seems much more useful.
I hope some of y'all find this useful, and look forward to reading other ideas and opinions.