Alright so my IDE is back up and running. I was given a solution by a helpful staff member in the CS50 Reddit Community, and it looks like i installed Flask on my own. I did remember actually installing a later or sooner version. It was part of a project's requirements.txt file.
But i'd like to thank everyone anyways for helping me solve the problem!
From your comments, you are using an older version of the appliance. Consider upgrading to the latest one, by removing this one and installing the latest from here: manual.cs50.net/appliance/2014.
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One way to fix this is to manually set the clock in the system settings for the appliance.
Down in the bottom left corner of the appliance go to menu > settings manager > time and date.
Set configuration to manual and then set the current time.
Worked for me after making these adjustments. Hope this helps.