Jet @dnorthrupva,
Not sure I can answer all the above but:
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that experience you mention is happening in the default group still. Behind the scenes it should be finding your devices. If you go to the entities section in he Dev Tools you’ll find the new discovered players.
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AFAIK yes. I do have web server enabled in each Kodi (currently 5 at home) … Not only for HA but also for remote control.
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check this: Allow dynamic visibility of items in UI
Hope this helps a little.