Ya man ,
Pittsburgh DNA… lots of philly buddies.
The expansion board is the truth(I have two 
)…Works with all the Xiao (except some swd stuff with the C3 AFIK)
check out the Magnifier and BLE , or ESP32S3 for stuff and here is a post and video of some goofing around, pointing out how you have to select the device each and every time to upload to it, and the IDE’s lack of basic Upper Case LC device names for searches.
there is allot of smart folks here willing to help, So jump in the water is FINE 
I’m in Hollyweird (hollywood). Still have family and friends in the burgh though, I visit when I get tired of that LOUD ass Latin music 
for a few weeks and run when it gets cold 
HTH
GL 
PJ
ps my younger brother did the Groton conn. bootage. He’s a Proud Navy Man. LOL