I have a form with file upload capabilities and I would like to be able to have some nice client side error reporting if the file the user is trying to upload is too big, is
You can do this type of checking with Flash or Silverlight but not Javascript. The javascript sandbox does not allow access to the file system. The size check would need to be done server side after it has been uploaded.
If you want to go the Silverlight/Flash route, you could check that if they are not installed to default to a regular file upload handler that uses the normal controls. This way, if the do have Silverlight/Flash installed their experience will be a bit more rich.