Played this with some friends last weekend, and we had fun.  We played for about four hours and developed around 200 years of history, mostly about man-eating hill crabs.  People had a lot of fun memeing about what was going on, everyone stayed engaged throughout the game, and the turns felt like they were a good length of time.
At the end, we felt like we hadn't ended up developing the settlement all that much.  We started with an intentionally small one to make room for that, but most events focused on something too narrow to make general growth possible.  Also, the events felt disconnected from the timeline: we had to force ourselves to think about how much time has passed, and that passage didn't feel very impactful.
That said, the core concept does seem solid.  We're thinking of playing a home-brewed variant of this where instead of items there is a focus on people, and with a different set of event cards.