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You just have to wait, eventually one of the people on those settlements will give you "the" alliance quest.
Go to each place and see if one of the settlers stands facing you and tries to walk towards you/follow you, they'll be the ones that will give you a quest, sometimes you can walk up to them and start a conversation and they'll feed you the quest.
The Slog and Warwick will join on their own if you talk to the NPCs. Warwick is even easier if you do the Atom Cat quest to fix their pump.
Country Crossing, Nordhagen Beach, Somerville Place, and Obelrand Station seem kinda glitchy on whether or not they will ask for help on their own. Talkign to Preston will definitely give you those though.
The other thing is Preston will only give you one quest that results in a settlement joining you at a time. This is usually along with another quest to help some settlement. Which is why it seems like Preston spams missions.
The other thing I noticed is some of the gain settlement quests almost seem level oriented.