VBScript does not support random/index access to the elements of the .Files collection. You'll have to For Each loop, pick a random file, and Exit the loop.
Update:
According to the docs, you can use a 'name' (file name, file spec(?)) as parameter to .Item(), so you could keep an array of file names/specs, pick one randomly, and access the file. Whether that would be an improvement in your case, remains to be seen.