Disk Space
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Solved by Ptopman,
I've already used CCleaner multiple times, however, it still only removes 1GB tops, still leaving very little free space on the SSD.
Are the folders related to the OS supposed to keep growing in size? If that's the case, should I look at purchasing myself a larger SSD?
Its going to be windows updates. Unfortunately 40GB is too small to be a boot drive, at a min it should have been 80GB, and that is pushing it. This is coming from a guy that did this when he wanted an ssd.
A program that is really nice and lets you see what is taking up space is called WinDirStat. I would recommend running it and seeing what files are taking up the most space on your drive.
If you get a new SSD, I highly recommend something that is 128GB or bigger.

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