tough call, I have worked for seven different 135 companies, and about half carry the same idea as YIP. The main thought being that one cannot plan on exceeding 14 hours...
Drunk passengers being late, Teterboro weather delays, ambulance getting lost to some podunk airport, a random aircraft with a blown tire that shutdown the runways; all rumors of situations that may have caused exceedence of duty times.
First of all, drunk pax shouldn't be allowed to board which gets into other problems, so flight cancelled.
With regards to the other excuses, if those cause you to block out knowingly to exceed 14hrs than that is violating the reg. You the pilot would be accepting a mission that is violating .267.
"Legal to start, legal to finish" is for the birds. Its an old timers mentality and its time to hang it up!