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I start to look into cleaning mine up when it gets to the 75%-80% mark. I don't tend to do it until I physically can't fit anything onto the hard drive or, if I'm on windows, get that annoying little message saying that I have x amount of space left.
When I actually do need to clean up my drive/s though I tend to just look at all the movies I've crap I've downloaded and used/watched once or twice and will probably never watch again. Most of the time that clears up a couple of gigabytes, but if it's still not enough I'll either move things along to external storage or go on a mass clean up and remove anything I don't need/want.
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"I am confident that if anyone actually penetrates our facades, even the most perceptive would still be fundamentally unprepared for the truth of House Dimir." - Szadek, Lord of Secrets
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