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(+2)

Yep! Most of the files will clean themselves up, but you can clean up leftovers once the process is complete.

The relevant files are AES encrypted with your device's unique ID and the selected password for every step of the process, so it's fine to leave them there as well.

Do I need to re-do the pairing process every time? 
It seems to reset on reboot, is it just me? 

You should only having to do pairing once! (On some devices, you might need to click 'Allow' to enable ADB-wifi on reboot - but that's just a single click)

Please get in touch on Discord, so I can help you with this issue.