The 65 percent and time out error is generally failure to accept the RSA Encryption key
Reboot your watch by holding down on the power button for about 15 minutes until it says rebooting
Restart your computer to be sure all caches are cleared
Check that developer options and debugging are enabled on watch (they should be but check)
Connection is made to Wifi it isn’t automatic but always on.
Change your watch face to a factory installed watch face
Launch GWS wait a full minute for it to be fully loaded
Select Run on Device and your device
Observe your Watch like a hawk and when the RSA Encryption pops up OK it
It should then load and run on the device.
If it still fails then you need to create a new Distributor Certificate.
If that fails you probably will get a different error message or it just hangs if that is it let me know.
Ron
Samsung Developer Relations