2. Special possessions
The next step is to establish each character's special possessions, and how they contribute to the village. During this round, you're trying to figure out where the PCs fit into daily life.
Almost everyone in Stonetop helps in the fields, at least during spring planting and fall harvest. Most of the crops (beans, potatoes, barley) get stored in the granary and doled out as needed. Folks keep their own homes, with gardens and small livestock.
A dozen or so folks ply the Great Wood. There are only a few full-time craftsfolk: a publican, a potter, a tanner, a smith, and a midwife. Other crafts (carpentry, weaving, etc.) get done on the side, by whoever has the skills and the tools. Most trade is based on barter, debt, and honor.
Have the players go around and share their special possessions and how they earn their keep. Most players will naturally tie their possessions into how they contribute to the village, but if they don't, press them on it.
Ask the questions below, plus whatever else you're curious about. Take notes, and update the steading playbook as needed.