This is why. The latest versions of OctoPrint are python 3 only and you are on an octopi version that doesn't support python 3. The best thing you could do would be to create a backup (if that's even available in 1.4.0), download that backup zip file and flash the latest octopi 1.0.0 that includes the latest OctoPrint 1.9.2 using the Raspberry Pi Imager.
Thanks! Yeap that exactly what I started to do earlier, I figured im so far behind I need to start new. Trying to do a backup, but it just seems to work for like the first 3 mins, then the server goes off and doesn't let do anything. Is there a way to do backup via Winscp? If not ill just start over fresh.