My queries both contained a "flu-like" cluster of symptoms, which can be challenging because they're associated with so many diseases. I tried to include some specific hints about geography and time of year that a physician would probably pick up on.
Not too bad. This case was indeed Lyme Disease. The AI system seems to have picked up on the geographic references -- northeastern US, and ticks in wooded areas.
I note, though, that the AI system invented some symptoms for Sally. Sally did not report that she "felt better initially but experienced continued pain later on". In fact, that was not true for Sally.
This case was COVID. From what you've said, the training sources were older than the emergence of COVID, so it's forgivable that the AI system didn't know to consider that. Influenza is a good guess, but influenza is rare in the summer (that's one reason I included a date). Lyme Disease would have been a reasonable guess again -- the date is summer, and there are still ticks in the woods. I'd say that either Lyme or one of the many respiratory viruses would have been a better guess than Bipolar or Depression.
So: I think the results here are comparable to googling one's symptoms, but my physician isn't out of a job yet.