I'm not sure about your situation but I feel most lay people are clueless about grad school and have very rosy views about it unless they have done it. Until classmates from my undergrad finished their PhDs I didn't realise how much politics was involved, for starters. And a gem they often hear is "It's easier in Ireland" in reference to difficulties getting lecturing jobs in UK (complete BS, it's harder in Ireland). I noticed similar things with my MSc where people seemed to think I could do 100 million things with my MSc (wrong, it's a specialist MSc).

Again unsure about the specifics but your T shouldn't be so crutched by her inexperience in your area, whether it be in relation to careers or cultural stuff. I once met a T that thought he had solved a career issue I was having within 3 seconds of the start of the session and as I re-explained specifics on my career he wasn't getting he started tutting about me as if I wasn't there, not bothering to hide his baseless contempt for me as I kept pointing out his errors. But my last 2 Ts were very good at not making thinking errors, even when encountering specifics they were not familiar with. It was like they'd slow down at the right moment and just listen, and the main one I used for a year would take notes and read up on what I talked about and took care to ensure old impressions of my career were buried (ie I rarely found myself mentioning an industry specific one week and find I had to re-explain it another week).