I remember the Amiga 500 being extremely cool in the UK, the essential gift for teens in xmas 89/90. So I'm curious about the context where for Dominik Diamond it was uncool.
You also have to bare in mind that home computers are more likely to have been “cool” (which, after all, is a subjective term) to people within the HN echo chamber than it would have been to the average person.
It’s also very likely that Dominik is talking about the Amiga being uncool just to wind a few people up. He is infamous for being a windup merchant. You only have to watch a few episodes of 90s Gamesmaster to see that.