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Looks like it starts on the 11th:
Most likely scenario in my mind is you are running out of process memory on the webserver (not physically, but against a php set memory limit) and that the file you are trying to upload is rather large.
That doesn't explain this symptom: "If I delete some old files, it lets me upload new ones again"
My guess is that the WordPress uploads are aren't respecting @CB's disk quota. Maybe because they are owned by a general Apache user on a shared host and the Apache user's quota is full? That would be something for your hosting provider to diagnose.
Maybe TF2 will finally get a competitive scene with tournaments of consequence, like CS:GO.
"Estimated delivery: September 2015"
They better not miss it, my anniversary is in September.
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