Update:  I have found the source of my problem.

I had a custom script (related to dynamic DNS) in /etc/network/if-up.d/

The script was failing, and as a result, the DCHP aquired address was
not getting assigned to the interface.  It appears that if any of the
if-up.d scripts fail, this will interrupt the correct operation of DCHP.

Additionally, i still get the error "SIOCSIFFLAGS: Cannot assign
requested address".  I do not know why... this indicates some kind of
failure, but all IP configuration is completed as normal. I have DCHP on
eth0, and a static IP addr on eth0:0.

I apologize for the noise, as it now seems my trouble report is not
related to the problems described by other contributors.

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'SIOCSIFFLAGS: Cannot assign requested address' when setting up ip alias
https://bugs.launchpad.net/bugs/123773
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