Well for 2), it clearly looks like a case of negative caching (dnsmasq
has no upstream server, therefore it only uses /etc/hosts only, if the
entry isn't in there, it considers it a NXDOMAIN), upstream also seems
to be aware of that behaviour as they offer the option to turn off
negative caching.

Anyway, I personally don't really care, I just want to confirm that this
isn't related to what we have in a default Ubuntu install.

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https://bugs.launchpad.net/bugs/1172467

Title:
  Dnsmasq caches negative results if it starts before the network is up

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