I didn’t get the issue on deleting files or empty trash issue on Mac OS X before until recently. It becomes as difficult as Windows, but however I found method to delete any Windows file by using a tool called “Unlocked”.
As on Mac OS X, the only solution seem to be boot up in Safe Mode and doing the deletion without any crash. So during the boot up, hold down the “Shift” key until the boot up loading icon appears. Then the progress bar will appear. After that just like normal access to your account to do the deletion.