Supply lines are both easy and somewhat confusing so just a few quick tips and hints which are not explained at all or very well in game -
0- Supply lines work any combo of connections that hooks up a settlement into the 'grid' of supply lines. You do not need supply line from/to every settlement. Just one connected line - think of it as a 'road' - if you can travel from point A to any other point connected by a 'road', all settlements along those roads are connected to all other settlements for sharing purposes
*exception - supply lines only share supplies and ability to scrap down at any connected location whatever breakable objects in order to pass raw materials. Constructed items like weapons, armor, furniture, are not shared as common inventory being supply lines.
**note - auto scrapping only scraps junk, items that break down into good raw materials (road leathers, clothing for cloth+leather, etc are not auto scrapped and are not accessed via supply line either
1- When setting up supply lines at first, you will almost always be starting from Sanctuary as first 'home base' till you decide to maybe move it later. So most players I expect end up sending settlers turned into provisioners (aka supply line assigned) from Sanctuary to other settlement.
Tip- start this way, but soon as you get 2+ settlements, send the newly arrived settler from Sanctuary to the other settlement - goto other settlement, meet that settler you just sent over, and then setup supply line from that settlement to Sanctuary. You want to setup reverse direction supply line to your main base because eventually you will setup all your big shops, at least until you can afford shops everywhere, at your main base.
Shops take manpower, and if you have 6 settlements and sent supply line people out from Sanctuary to those 6, you just used up 5 settlers and your 'main base' starts to have lot less available manpower than a smaller, non-main base settlement. So to avoid re-doing all your supply lines later, just start out hooking up from Other settlement --> Sanctuary or any other settlement that allows hooking into the 'grid'
This way the population hit goes on the other settlement, not your main base
2- Supply line help text is frustratingly minimal and it does not tell you that you can not setup supply line from A to B, unless the location you are sending supply line to is NOT maxed out on population (charisma + 10)
This is weird because the provisioner counts against the population already of the place you are sending from, so why does it matter that where you are sending TO is maxed out or not?
Don't know why but if location you send supply line to maxes out AFTER you send supply line, all is well. If it is already maxed out, the UI removes that location as a place you can send supply line to.
So juggle people around by playing musical chairs if you need to , in order to hook up a settlement that is already maxed out
3- Learned the hard way that supply line provisioners can be attacked - they are far as I can tell, never attacked when 'off screen' from your location- BUT - they load into the game kinda like how skyrim does if anyone remembers - there is some config I am sure that controls the X number of nearby cells to load for game state. So whenever you travel somewhere, any provisioner within that X load cell distance gets loaded into the game.
This is when they can and will be attacked, or they will stupidly go running off to fire on some harmless insect and run into a mutant pack.
So the only settlers that I try and actually arm with hand me down good weapons and gear are my provisioners as they are the only settlers that face trouble alone in these scenarios. You'll hear shots so you can go run to help them, but decent gear lets them live long enough for you to get there.
4- This isn't a settlement issues thread so won't recap - just remind that the UI display for how many people are at a settlement is bugged. The cap is charisma + 10 for population but people claim they have more - because of this bad UI. Sometimes, your presence plus companion will push that count up by 2, sometimes it will be lower than really is.
The one and only way you can ever know how many settlers truly are in that settlement due to bizarre wrong/bugged UI, is build a bell, ring the bell, count all the people that show up and add your supply line guy if not already there as the bell doesn't summon him if away from settlement.
5- Supply line people are the only settlers that don't animate or show idle post state of sleeping. They are quite literally always on the road, your hardest working slaves that never get a break. But for settlement happiness purpose, they take a bed.
Hint- if you just can't figure out why your settlers complain about having to sleep in shifts but you are positive you assigned beds manually to ensure everybody has a bed (due to settlement issue you can have 100 extra beds but settlers will not get bed to sleep in unless you manually assign sometimes) - make sure to check you assigned your always on road or standing around settlement supply guy. He never uses it, but he still takes a bed in the settlement where his population counts.