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If I was sure I could achieve this then I'd do the same. My 4090 FE has treated me great for 2 years and even selling it for £1200 meaning the 5090 essentially costs £800 feels worth it for 2 years of assured great performance.I have a 4090 and will upgrade to a 5090 - But only if I can get a FE or card at MSRP.
I should get £1400 for my 4090 hopefully which means the upgrade is £600.
If however I can't get a card at MSRP then I simply won't upgrade as not going to pay over £2k for a GFX card.
It was pretty easy to pick up a 4090 FE in Jan 2023 when I got mine so I'd expect at least around the spring of '25 it should be easy to get a 5090 FE.
Making me think this is when I'd get the best value for my 4090 pushes me toward it. I've also got a monitor that supports DP2.1 which the 4090 doesn't so it would be good to add it for that.
Waiting a generation worries me as well. Buying a 6090 in '27 would have been concerned that a PC built in 2023 would be bottlenecking the card...