Seeeduino XIAO expansion board on Arduino IDE 2.0 beta - Live Debugger issues

I know that this is not a answer to your very question to enable XIAO debugging with the Arduino IDE. But if you are willing to try PlatformIO I can confirm that debugging with the J-Link adapter works.

Set platformio.ini to:

[env:seeed_xiao]
platform = atmelsam
board = seeed_xiao
framework = arduino
upload_protocol = jlink
upload_port = jlink
debug_tool = jlink

Then set a breakpoint in your code.
Then start debugging:

When it stops click ‘Restart’

When ist stops again click ‘Continue’

Now it will stop at your breakpoint