How to 'view' multiple (or one) pin states as Watches

No worries, no apology necessary.

If you google that, with ESP32 tagged on, you get quite a few hits. Does this give you anything you recognise? A problem internal to GDB has been detected esp32 - Google Suche

Failing that, what device are you coding for? What debugger are you using? Are you able to post your zipped up project somewhere – assuming non-confidential – like Dropbox, Google Drive etc?

I’ve got a few microcontrollers around including an Espressif D1 mini, so maybe I can recreate your problem?

Cheers,
Norm.