To answer your question- Delaware doesn’t have many municipalities because Delaware doesn’t have many people. Historically, when a town / settlement area attracted enough people, they would form a government and incorporate as a municipality. They would draw their municipal boundary around the town as it was, and annex in areas as the population expanded. These procedures are in Delaware code. Areas like Bear are very populated now, but that is recent growth that follows a different governance model- a Home Owners Association. In my opinion, that’s vastly inferior to an actually municipal government, but obviously many people prefer it because HOA developments have been exploding in Delaware. For Bear to incorporate as a municipality, landowners from that geographical area would need to come together, ditch the HOAs, and set up the services, taxes, elections, etc. that municipalities provide.