@Justin I’ve run into the same issue at times. I just wanted to write and recommend listening clearly to what duwudi is saying. It’s just a test to verify that the issue isn’t hardware.
I immediately thought it was hardware myself and then I reloading a fresh install of the OS and the OLED started working normally.
I discovered that something in what I was doing with the OLED in my code was causing a loop that never stopped and it took over the OLED from returning to normal behavior.
It sounds like you’re think that he is saying that every time you have an issue with your OLED that you’ll have to reflash the OS and start over. I get it, I thought the same when I ran into the issue. But what a new install of the OS helped me discover is the OLED was fine on my pi-top and that it was something I was doing in my code changes that messed it up in the Python call for the OLED driver. Even if a reboot of the pi-top was done it wouldn’t work right. So run the install of the OS again and if your pi-top OLED starts working, you know hardware is fine and it’s a software issue.
Just my couple pennies worth.