The idea of a privacy checkup session is smart. I read somewhere that a lot of older people just don't realize how much they're sharing by default. Maybe it's just me, but showing them step by step seems like the best way to go.
My aunt posted her new debit card online last year. It's not about being careless, they just see it like showing a photo to a neighbor. I sat down with my mom and we went through every single privacy setting on Facebook. Took an hour but she finally got why her vacation posts were a map for burglars. The default settings are the real problem, they're set to share everything.