I'm really not all that far into my first game (@30 hours at this time), but I have discovered one very, very important gameplay tactic that I wish I knew in advance. That is, gathering resources for settlement building. I went gathering-crazy in Sanctuary, planning to build that ONE settlement up into a city if at all possible. With that in mind, wherever I went where I could use a workbench, I gathered EVERYTHING.... and then schlepped the accumulation back to Sanctuary. That meant if I ever planned to build up places like Abernathy Farm or Starlight Drive-in, I would have to schlep those resources back to the locations where I had originally collected them.

So, Word Of Advice: Leave gathered resources where you gathered them. (The Red Rocket gas station site being a notable exception.)

I have only 3 places that are of interests to me.

Santuary

Abernathy farms

Red Rocket.

These 3 are close together and in the corner of the map. May start sending people to the ones with less or no people.

Just wish I didnt have to micromanage everything. Also I believe if you gain local leader you can link each settlement with caravans.