21 wroteIs your current CPU holding you back at all?
If yes, consider an upgrade. If no, don't bother.
Only real upgrade from a 5820k would be something like an i7-8700k/9700k or i9-9900k IMO (new motherboard makes the i7's more of a sidegrade really- and the i9 is hecka expensive). Ryzen isn't really going to be an upgrade from a 5820k, unless you go Ryzen 7 for 2 extra cores, but then you'd need a new mobo and you'd probably be better off grabbing a used 5960x/6900k anyway if you wanted an extra 2 cores.
I'd maybe add another SSD. 256GB isn't huge, and you can get 500GB 860 EVO's for like $70 so no reason not to add one IMO.
I wouldn't bother spending all that money on an RTX 2080Ti right now to use it with 3 pretty mediocre 1080p monitors tbh. I'd just hold off until you can upgrade monitor(s) and GPU, especially considering how terrible the GPU market is currently.
When you say moving to 1440p, do you mean 3 x 1440p 60Hz monitors? Might be worth considering 3440x1440, or 1440p high refresh rate. You could get an RTX 2080 and a nice new 3440x1440 100Hz monitor for less than an RTX 2080Ti;
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My current CPU is only using about 40% when I play GTAV on high settings(at max spikes).
Whereas my GPU idles at 98-100% usage and causes FPS drops.
As for my monitors, I like the idea of an ulttra wide but I'm a stickler for multi-monitors. I do a lot on the side that I need at least the second monitor for. YouTube, Netflix, Forum browsing, Etc.
I'm also a stickler for special stuff, so I tend to look more towards the Ti, simply for bragging rights.