Thanks for playing!
I think the biggest issue was that I didn't explain the medicine quest clearly enough. While watching the stream I noticed you mostly used the regular talk option and never really asked people about the medicine. The idea was that NPCs are busy with their own problems, so they won't bring up Rare Medicine on their own — the player has to start that conversation.
Looking back, I think "Ask About Medicine" was probably poor wording on my part. It sounds like an optional question, while it was actually the main way to progress the cure quest. Something like "Talk About Your Illness" would probably have been much clearer. A small tutorial would have helped too 😄
As for the robberies, sleeping outside is always dangerous, but getting robbed while scavenging is only a random risk event.