Hi there,
Well, No not exactly . That technique (what you are describing) is used for 2 special situations. Say’s so HERE…
BootLoader Mode
There are times when we use the wrong program to make XIAO appear to lose ports or not work properly. The specific performance is:
Connected to computer, but no port number found for XIAO.
The computer is connected and the port number appears, but the upload program fails.
When you encounter the above two situations, you can try to put XIAO into BootLoader mode, which can solve most of the problems of unrecognized devices and failed uploads. The specific method is:
Step 1. Press and hold the BOOT button on the XIAO ESP32S3 without releasing it.
Step 2. Keep the BOOT button pressed and then connect to the computer via the data cable. Release the BOOT button after connecting to the computer.
Step 3. Upload the Blink program to check the operation of the XIAO ESP32S3.
Keep reading the wiki , the next section. You’ll see
The Normal way is to Hold the Boot button down and TAP the reset. You don’t unplug Anything.
I mean it does make sense right. Why would you unplug just to Download, Gosh just pressing the button some times is enough, When it get’s bad code 
do you even need BL mode.
HTH
GL 
PJ 
FWIW, on the serial monitor it will say waiting on Upload , yada , yada the current code will stop running and enumerate the serial port.
Currently , Your ESPtool is losing the com port with all the “…” then error. 
