Let me address several of your questions and/or points:
I have an 8700k which I haven't yet overclocked. It has an AIO cooler but the InWin case has ****ty cooling. I still need to install three intake fans on the bottom. Right now it has the AIO fan as exhaust out of the back and 3 120mm fans side mounted at the top. It's too bad there was no front intake as the rest of the case is totally empty and has nothing restricting airflow. I really miss my Coolermaster Storm Sniper. I'll attach pics.
I definitely would prefer a VA or IPS Panel. Not sure which is better for a performance/quality standpoint. I play FPS's but not competitively whatsoever. I like stuff like far cry more than spending hours on end playing multiplayer. I have enjoyed battlefield though, I just suck at it lol. I'm not an eSports gamer by any means so 5 ms is plenty fast.
I don't have to hit 144 Hz consistently, just want enough to notice the difference. 100 hz would probably be fine, 120 would be great. Freesync is a must and the G-Sync certified moniker is pure b.s. marketing speak. Their list of 12 certified monitors are almost all 1080p monitors and all are TN panels. No thanks. If you can enable free sync it will work. The variables in the performance of A-sync are in the quality of the monitor, not with how "compatible" it is.
32 inches would be great only because I've actually seen ones in that price range but 27/28 is perfectly acceptable.
I'm OK dropping some settings to extend the life of the card and usually drop down to 4x MSAA anyway. I'm happy to listen to suggestions on other settings I can tweak to improve performance as long as it doesn't lead to a significant hit in quality. (As dumb as it sounds, I do like my hairworks enabled, one giant ponytail bouncing around with nothing else moving annoys me for some reason lol)
Ideally I'd like to max out as much as I can now and be able to squeeze out high settings if possible in 4 years or so when I'm ready for a new build. Because there's no way I'm spending $700+ to extend the life of a 5 year old platform at that point. I miss the days when $400 for a high end card like the 5870 was way too much. I was able to build a top end machine for $1,350 back then.