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Not too sure about whether you need to read them all in one playthrough though but better to err on the side of caution.
I already checked and there was only "issue 2" there.
What you can do though is start a new game and just skip text and turbo mode so that you can read Issue #1 and see if that contributes to the steam achievement progress.
That's what I was planning to do, and I totally forgot about turbo mode, thanks, haha.
A bit of thread necromancy here (apologies) but I couldn't find the answer anywhere on the Internet, either, so I needed to come back and let everyone know definitively that NO! You do NOT have to do it on the same playthrough to count towards the achievement. I was in Chapter 4 trying to figure out how to get a save editor to work because I missed issue 3, and when I spent hours doing it only to have my game overwrite the altered save file every time, I looked back at earlier saves. I saw I had one near the end of Chapter 1, loaded and played it long enough for Issue 3 to become available, bought it, read it, and boom! Suddenly I have 8/10 issues read according to the Worldly Reader achievement tracker.
Hope this helps someone who stumbles across this in the future to avoid hours of replaying.