You always roll to the latest?
It really depends. I won't usually spend a ton of money on new hardware unless there is something to gain from it. I tend to skip product refreshes as the cost vs. performance gains over the initial architectural release is usually too small to bother with it. For example: I stuck with my 3x 8800GTX's rather than upgrading to 3x 8800 Ultra's. The difference in performance was almost negligible and the cost to do it would have been insane, even factoring what I could have sold my 8800GTX's for at the time.
However, I went from a 2080 Ti to a 3090 without a moments hesitation. I am not likely to upgrade to whatever NVIDIA's 30 series refresh is as I doubt the increase will warrant laying out another $1,500 or more. Whatever comes later will be in my sights for sure. In contrast, I ran the Intel Core i7 5960X for almost five years. The 6950X was almost 50% more expensive for two more cores. The IPC uplift and loss of overclocking headroom made that upgrade a wash for playing games. It essentially served zero purpose to buy it. Mainstream CPU's weren't all that enticing back in those days either given they were quad cores. I have always run high resolution displays relative to the vast majority of people. I didn't care what a 7700K or something like that did at 1080P.
The only reason I really went with the 10900K is because I was planning on buying a new CPU anyway. It was time to upgrade my girlfriend's machine and I needed a CPU. So, I gave her my 3950X and bought a 10900K. I wanted a 5950X but for my purposes (gaming) the 10900K is functionally just as good. Especially since I'm running a 4K display. That being said, if I 5950X comes up for sale and I can grab one for a good price, I may very well swap motherboards and CPU's with her and sell that 3950X.
