This sounds very similar with what we went through.  many of our daily 
schedules were configured for "1 day", and for some reason if a backup started 
and completed very close to the end of the backup window, it would wait for 
around the same time the next night.  Depending on how busy the environment 
was, this job would then either fail because the backup window closed, or not 
start at all.  

I forget where i read this but the suggestion was to change the frequency to 
something like every "20 hours", where it was actually tried and start the jobs 
earlier.  This has seemed to help in our environment.

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