Can't thank you enough - the solution in here for me was manually connecting the watch to the same wifi network my phone and laptop were on. After that I had to toggle developer mode back off and then on because it failed to detect that developer mode was already enabled but after that final restart (and another Xcode reboot cuz ofc) everything finally connected properly.
phil@tryfi.com
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Where can we view information/possible workarounds for this known bug?