Does an installation over existing version require you to turn it back on because I haven't had to do that for the last 4 upgrades.
Yes atm it should require you to turn it on (if you use "automatic" option)
100% works for me without activating it after upgrades (aside from the process of me having to force HDMI on audio the first time).
thats by design since not everyone will get a good exp with audio on hdmi (pizero2w, pi3 users etc... its a choice but when its on it stays on)