I went through a similar transition and ended up with yabai + skhd for tiling. The Dock pain is real.
One thing I'd love to see: integration with tiling WMs. Being able to see which windows are in the current yabai Space, and maybe even switch between stacked windows, would be amazing.
Does boringBar play nicely with yabai or similar tools?
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Technically it should - I tried using Amethyst with it for a few weeks before launch and it seemed to work fine for me.