In the mission "Talkin about a revolution" with the Judy/Clouds sidequest, I tell her about the chip in my head and how it is killing me. Didn't I already tell her this? I swear I did... Well, she is surprised again.

When my wife tells me something, I'm usually surprised even though she claims she had told me that before. So that's +1 to realism.

You've got a wife really ?.

I had the same reaction but then recalled in my playthrough that I had said "it's a long story" the first time this came up (mention that Johnny is somehow relevant to our heist) instead of actually explaining this dude was in my head

You probably did :)

Because the same thing happened to me. I told her everything about Johnny and what an engram is and got in the later quest, where you are, only prompts to tell her again like it is the first time.

There is also some inconsistency with Judy later in her plot, at least when you play male V (so no romance, haven't tried female yet). The devs have been a bit sloppy here...

One of the fixers tells you something like "If you had more Street Cred" you'd know ... or something like that. I was already maxed out.

Happened to me as well. I'm a 100% sure that I told her about the engram (she even whistled) and later, she acts so surprised by the fact. Anything outside the main quest and Silverhand is poorly done.

She's got a lot on her plate, so you must repeat the same things a few times to get through.