Which worked pretty well, at least at a quick glance. I wasn't sure what to do whoever, so I instead opted to build a caravan so that it could use Sanctuary's resources to build itself up.
Instead no one did anything and stood around for I wanna 20 hours (Real time) before I decided to manually finish the job. My settlements struggled to develop early, so much so that the settlement I used for 'Who can? Asam' had me thoroughly confused : The quest seemed to imply that I could set a mayor, pick a plan and stuff would just work. I've recruited many settlers, half of which are vanilla ones, the other half a staggering amount of SS2 unique NPCs. I've let SS2 mostly run on auto-pilot since the beginning of the game. Feel free to rant with me though, might make me feel better and less dumb.
I dunno, I don't want this to be a rant topic, I just needed it off my chest. Let me explain, though feel free to skip to the TL:DR if you don't wanna read the 'blowing off steam' part.