Verbing nouns since 2011
So I'm on my second playthough and i was wondering if you always have to play a random settlement event card every year, including the ones that already have a story event in it like burning hands or armored strangers.
Yes, always draw a random settlement event when returning.
It is possible to have a random settlement event, as well as a few other 'scheduled' settlement events that trigger from previous years and hunt events (lights in the sky & murder come to mind). You could end up resolving 4 settlement events in a single year. Just make sure the random settlement event comes first.