Yep, I think we're being too attentive landlords because I encountered the same soft-lock.
This happens in part due to a too-small pool of written requests (ran out of time to write more before the jam ended)
While it probably won't produce requests as good as "talking trees" (lol), this seems like the perfect use-case for an LLM. Generating requests on the fly during gameplay or even just for your request lists in `requests.json`. With a proper prompt and some examples you could generate limitless requests with little effort (although guaranteed lower quality than your hand-crafted ones).