Build Advice I think its time to upgrade, need some advice on what Ive picked out

Jan 25, 2020
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Why Are You Upgrading: I'm having big FPS dips, hang ups or even crashes in games like Borderlands 3, Resident Evil 2 remake, etc. even on low settings. I figure my CPU is fairly old, plus not overclocked. Im not sure if OCing now is something that can be done, I have no experience with it. Would just like to run more modern games without issues killing the immersion. I play a lot of shooters so upgrading to a 144 Hz monitor would be nice. I'd like to know if what I've chosen makes sense or if I should go another route. Thanks!
Approximate Purchase Date: This week
Budget Range: 1000-1200
System Usage from Most to Least Important: Gaming
Are you buying a monitor: Yes
Parts to Upgrade:
Current build
i5-2500k @ 3.3GHz
Cooler Master 212 EVO
ASRock Z68 Extreme3 Gen3
Corsair Vengeance DDR3 @ 1333MHz (4x4GB)
EVGA GTX 1060 6GB
Corsair HE650W psu
SanDisk 480 GB SSD (System installed here)
WD 6400AAKS 640GB
Seagate ST3000DM001 3TB
Cooler Master HAF 932 Advanced case

Thinking about upgrading CPU/MOBO/RAM combo to:
i9-9900k
GIGABYTE Z390 AORUS PRO
Corsair Dominator Platinum DDR4 @ 3200MHz (2x8GB)
And instead cooling with Corsair H100i PRO

Preferred Website(s) for Parts: Newegg or Amazon
Location: NY
Parts Preferences: by brand or type (e.g.: I would like to upgrade to Intel CPU)
Overclocking: Most likely. I had help with my last build as it was my first. Friends that helped didn't know anything about overclocking so I never messed around with it. My PC did what I needed it to do.
SLI or Crossfire: No
Your Monitor Resolution:
I'd like to upgrade to 144Hz, but I'm fine with only 1080p as I don't want a monitor over 24" anyway
LG 24GL600F-B currently on sale on Newegg
https://www.newegg.com/p/N82E168240...or&cm_re=144HZ_monitor-_-24-025-942-_-Product
 
Jan 25, 2020
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You should first figure out why your games are crashing and you have big FPS dips, because on 1080p named games should still run fairly good on the system.

I wouldn't recommend buying a i9-9900k and keeping the GTX 1060 6GB because it will strongly bottlneck the CPU in the most games. i5 2500k and GTX 1060 6GB should fit pretty well together in the most games.