Did you disable all firewalls?
Also, during usb flashing, the device boot up as a different device after the uboot is up, so you will have to go through the static ip setup again. Don't clear the other existing setting by the way, refer to point 34 on the http://processors.wiki.ti.com/index.php/Sitara_Uniflash_Quick_Start_Guide.
In your last screen shot, please switch to the status view and let's see what is going on there.
You could also find server logs in uniflashv3\third_party\sitara\log; Please delete existing log, recreate the issue and attach the log here.
I would also setup the COM connection if I were you, as we are not sure where it went wrong. The COM port will give more information on if we are getting responses from the board at all.
Thanks,
Victor