I'm very skeptical of using AI in this way. I've given Claude access to calendars and travel plans and asked it to do similar analytical tasks cross referencing documents that would take days for me to do manually. Since it was about my own plans and life that I knew well, it was possible for me to spot subtle errors that seemed correct at the surface level but actually weren't the conclusions I would make. I've attempted these types of tasks 10-20 times with similar experiences each time. In the end, it's made me very skeptical, like your wife. I don't trust any AI output without a thorough review. Hallucinations are still a frequent problem.