The only files I've moved from my computer to droid were icons for bettercut, once I opened bettercut I chose "pick picture" instead of using the bettercut icons and they were there with all my other pictures. I guess depending on which kind of file you're talking about you can open the app you'd be using for the file and then see if you can get to them from there.
Sorry, I'm new at this so I may be wrong, but that's my two cents.
Just open up the "droid drive" in windows. Then drag the file wherever you want. But if you are just dragging them to the drive, then they will be in the root of the /sdcard folder...
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