Haha! Wish I could tip more than once. If it wasn't for your response I wouldn't have gone down the other path.
Much appreciated!
raminf
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A lot of mentions of "Settings > Privacy > Developer mode."
Turns out, it's on the ACTUAL WATCH!
On the watch, pressed the crown, then selected Settings (gear icon). Scrolled down to "Privacy & Security" then scrolled to the bottom > "Developer Mode."
Toggled switch on. Prompted to restart. Answered yes to all trust questions.
Quit Xcode and restarted, went to XCode > Window > Devices and Simulators, then selected Watch. It went through fetching Debug Symbols, then it was good to go.
HTH.