I'd do it like a TV series with episodes. Each or a few episodes could deal with one of the conflicts that you have listed. The episodes could be spread part by a day or even weeks in the story, so that you'd see some progress in the outpost. For example, if the settlers were attacked by the bloodthirsty goblins in the first episode, they'd probably build defensive walls and perhaps a tower afterwards — or whatever you decide on — and then in episode two (a week later) the defenses would be finished.

You should go with a basic plot for each episode. For example, the settlers wake up one morning and tend to their daily things, someone sees a goblin scout and warns the settlement, the goblins attack and there is a fight, the settlers win and either strengthen existing defense or build new ones, end of episode.

I don't know if this helps, it's just how I'd do it.