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I've skipped the PS5 Pro. I would have skipped the PS4 Pro but my PS4 bricked and I bought a used Pro to replace it.
I had the Game Boy but didn't buy myself another portable until the 3DS XL Zelda edition. That is a purchase I regret as I bet I spent less than 2 hours on it.
I am just not into handheld gaming and while I have a Switch 1 and an S2 I do not use them in handheld mode. I skipped the PS portables for myself (I have bought most of the Nintendo and Sony portables for my son, just not for myself).
I was interested in the Virtual Boy until I played it at a store so I skipped that one too.

I will likely skip the PS6. My interest in gaming is waning and while I really like the UI and how fast the PS5 is I just don't play it enough.