I saw her suffering a psychotic breakdown and talked about it, I saw her taking a medicine and talked about that too. I've slept several times since then but I'm not getting the grandchildren recording bit. How long does it take for it to come up? I wonder if I could've missed it.

It happened for me the next time I slept, so I don't know. You won't miss it when it happens. It automatically begins playing when you get up, and lasts for probably at least 20-30 seconds.

It's been a while now, so I guess I'll have to use console to set a quest stage.

I was wandering around while it happened, I never heard anything about sleep triggering it?

According to wiki it happens after you've slept/waited after the medicine talk thing. But it doesn't say anything about how soon it's supposed to happen - right away or randomly?

Suppose it could be random, but, like I said, for me it happened right after I slept.

Don't know. Lily's quest is very similar to ED-E's, so it might require a set amount of "real" time to pass before you can activate the hidden triggers.