Depends on the person more then anything. Some are tech chasers and will upgrade every year, even if said upgrade doesn't really effect any real world performance. Some will upgrade as tech seriously improves. So an early curved OLED to a 2016/2017 model would've been a decent spend. Again with OLED, going from a 2016 to a 2020 will be a decent upgrade.
My last 3 tvs (2013-currently)
32" Samsung
55" 4k LG (first gen 4k!) - a pointless tv really, because I had it years before 4k discs became available
55" 1080P OLED
Each has been a significant upgrade over the other. Went backwards with resolution, but the OLED has a much better picture compared the crappy IPS panel on the LG.
Looking to upgrade again as the oled has developed the common dead pixel issue, and the screen uniformity has gotten worse over time.
Either 65" oled or 75/85" LCD depending what the sales throw up. Be hard to drop OLED blacks, so prob end up with a CX or Panasonic HZ1000.
Though a Sony 85xh90 for 2.5k is hard to ignore...