On Thu, Mar 6, 2014 at 2:30 AM, Donald Stufft <donald@stufft.io> wrote:
It’s not reasonable to expect that midnight will evaluate
to false, ..

Only in the world where it is not reasonable to expect programmers to read library documentation.  In my world it is reasonable to expect that the behavior that was documented in 10 major versions and for 10 years can be relied on. 

 
especially when it doesn’t if you happen to have a tzinfo on the time (sometimes!).

As long as tzinfo specifies a fixed offset, there is no problem with the current definition.  If you are unfortunate enough to live in a place with semi-annual DST adjustment, aware time objects are problematic for reasons that have nothing to do with the discussion at hand.