At what point does reading (even kana) get more 'automatic'?

It’s definitely a very long process, one that’s going to be a bit different for everyone, and unfortunately not one where there’s a single moment where BAM you can read. It’s just gradual.
My only advice is to keep practicing, try to notice your accomplishments as time goes on, and check out the resources for starting to read thread if you haven’t already: Resources for Starting to Read Japanese Content

This kind of thing is I think where graded readers are especially going to be helpful, if you can get your hands on them, since they’re specifically designed to help ease you into reading comfortably, but any practice is good practice and it really does help.

Looking back and seeing progress is really important because it’s extremely easy to say “this is still hard, I must have made no progress and have learned nothing” and sell yourself short. I still feel that way sometimes…

Please don’t use these specific time frames as any kind of comparison, but as an example of looking back and seeing progress, I like to look at the 3 years and change I’ve been steadily studying:

  • After the first year I could basically read a little bit, in that I stopped feeling like I needed to reread simple stuff like Yotsuba in English, even if I still took a long time to understand it, looked up lots of things, and didn’t 100% grasp every detail and grammar form.

  • After the second year, I could specifically seek out and read things I cared about, in that I could read a new volume of my favorite manga before it was translated and basically keep up (even if again, slowly and with lots of dictionary usage). Only around here did katakana really start to feel automatic, to be honest.

  • After the third year, all of that was reinforced, especially with long texts, and I felt confident enough to tackle anything in theory. I finished my first novel, Legend of Galactic Heroes, and it was much less painful at the end than when I started it.

  • The fourth year so far has been about speed - I suspect the milestone I’ll think of when this year is done is just the volume and speed of reading has increased dramatically, and I can finally feel the amount of dictionary lookups slowly ticking downward.

Again, I don’t mean that as a “time to beat” or a good or bad example, and keep in mind it all depends on your goals and what you practice (I focus all but exclusively on reading so listening does not feel automatic or easy to me the way reading does, and I can’t speak even a sentence). But maybe it can help give some idea of what the process feels like, and how you can spot victories along the way. When I catch myself thinking “I’m just picking up on context clues, anyone could do this” - I can run down those markers of progress in my head and feel better. And I think anyone in the process can do that too – you’re wanikani level 8 after all, and 100% there was a time when the characters meant literally nothing to you, and now that’s long gone!

So keep at it, and good luck!

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