1.) You can do that by uploading the files and after that, linking to them when adding them with Downloads II. However... you have to put in the correct link and the correct filesizes yourself manually. There is no other way.
2.) For your 2nd question I'm not sure. Is the name CoDWaW-1.2.-1.3-PatchSetup or CoDWaW-1.2.-1.3-PatchSetup.exe? In the first case the extension is too long I guess.
It is possible to use longer filenames, but I think there will be a limit to the length.
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