For most of summer: we set up a base near the Beefalo, farming using their manure. The base also contained a wormhole leading to a grassy field with rabbits. We fall into a pattern of one person going out and exploring while the other tends to the farms and the base; we're both (re)learning the game mechanics as we go and we both have little pet projects. I gather some thirty berry bushes into a convenient patch int our base, learning only fairly late into the process that I need to fertilize them. My friend builds a telltale heart and sets out getting spiders and pigmen to fight as a way to obtain silk, and baiting traps for rabbits. We're not exactly thriving, in fact we frequently come close to starving to death, but in the end the farms and nearby food sources are enough. We get a crockpot and I rediscover the glory that is combining a morsel and three berries to make meatballs.
Literally the first day of winter: We discover we built our base too close to the beefalo when mating season starts and two of them charge into our base. This turns out to be not that bad, because two hounds and an ice hound ALSO charge into our base. The hounds chase us around, snapping ineffectually at Chester, until the Beefalo charge in. In the ensuing clusterfuck, the two Beefalo annihilate the hounds. I dart in to grab monster meat and teeth that drop. Inexplicably something catches fire around the area of the fight; my beloved berry patch catches fire. I stare helplessly on, wondering if there is something I can do to put out the fire or if I should cut my losses and shovel a few of them up. The crockpot catches fire, despite being made primarily of stone, and burns to a crisp. The Beefalo still aren't done with their rampage; with nothing of value left in our camp, I call to jump through the wormhole.
The first night of winter begins with the two of us wearing nothing but spears and backpacks (and accompanied Chester of course) huddled around a fire pit in a new camp. Our only winter supplies were two thermal stones and two pieces of jerky. Both of us were starving, low on sanity, and seriously wounded. We spent several days scavenging the immediate area and trapping rabbits before running out of food and setting out to obtain more. Long story short, my friend was at very low health and got killed hunting multiple catcoons at once, and then her ghost drove me insane. But, if that hadn't happened, something else would have killed us for sure.