@johnnycurry Hello it appears that the remote may not have been in upload mode. Please check out this video it goes over how to upload a program to the remote. There are some key steps that need to be followed exactly in order for the remote to be in upload mode.

The timeout error usually indicates the remote is not in upload mode. (Blinking blue led on the right side & BLE module not flashing red)

The other possible error is selecting the computers internal Bluetooth port and not the /dev/cu..SLAB_USBtoUART

Please let me know if you have any other questions.