So my initial game .. broke. Turned out a script didn't engage and I ended up working for the wrong faction.. long story short, I started from scratch. This time I've decided to join the Minutemen and focus on re building the world.
So far I have 19 settlements under my command

all fortified to at least 80+ defense (with sanctuary having over 150), artillery, shops and enough beds/water/food for everyone. All connected via trade routes.

Here's the biggest structure I put up so far, there are shops on the ground floor, a chill out area on the 1st floor and the 2nd floor is my personal penthouse.
Honestly I thought all this sim postapo would be something I wouldn't get into.. and look at me now, a minutemen General with 19 settlements under my care and the 20th soon to be added - Spectacle Island.
Also, look who I met:

Yac.