I didn't mean that your specific device is necessarily doing that (dropping the preboot connection) but it can happen with some misbehaving soft-bricked devices and if it does happen then persistence (and both timing and luck) are required to complete a flash. You can observe the Device Manager list to see if it's dropping out of there then reappearing.
ALWAYS safe-name the RGN file using protocol XXXX01000xxx.rgn regardless of whether it's original, cure or quickcure where XXXX is the HWID, in your case 2050. Using 960 (xxx) for the applicable software version 9.60 being used is preferable but the numerals don't have to match, that's more about identification.
Unfortunately the inconsistency in flash results you are seeing might indicate internal flash memory damage rather than it's dropping connection for another reason.
Ditch the laptop and find a Windows PC with rear USB2 ports, even an old XP one will do as you don't need an internet connection anyway. It might solve your connection problems but you'll probably need to load Garmin Drivers to it. USB3 wasn't around when Garmin designed Updater.exe so it doesn't always play nice with Updater even though USB3 is supposedly backwardly compatible with USB2 cables and devices.
Best practice is to force the device fully off before trying again however if it's dropping the connection due to physical damage to flash regions rather than attempting to re-start (boot-looping) then nothing can be done to complete the flashing.
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