Thanks for the screenshot, because it shows a proximate cause for TILP failing to communicate with your calculator
TILP is indicating, in both the GUI and the terminal, that you're trying to communicate with the "none" calculator; the GUI is indicating that you're using the "null" cable. Those are placeholders which do not implement any protocol and do not attempt any communication operation.
The solution to this problem would be to try and configure TILP through the "Change device dialog", accessible in the File menu, by right-clicking on none -> null:#1, or pressing Ctrl + D. The list of devices near the bottom dialog ought to inform you that you can communicate with a Nspire, using the DirectLink cable.
In this dialog, be sure to check the "USB scan at startup" checkbox, for next time
Now, with that said... if no device is listed in the list of devices near the bottom of the "Change device" dialog, it's entirely possible that the version of libusb used by TILP II 1.16, even if it's a recent one, has a problem on Win 8
In such a case, please post here the contents of the ".tilp.log" file, which you'll be able to find in your home directory (presumably C:\Users\<yourusername>\).
Thanks in advance