And does comprehensive cancellation insurance counterweight the decision to take the cheaper alternative flight and cover off any financial loss I may incur from not being able to attend work? 
Short answer – no…. I estimate one day of lost wages removes any financial benefit I might gain from the cheaper flights. Therefore I am going to continue to take my more “expensive” option and incidentally access to the bubbles in airport lounge!
I am a complete airline snob… I tend to pay a little more than the average person when I am booking short duration trips. I have always used the excuse that the airlines I use tend to us have the least number of cancellations and I won’t miss work, however today over a post-gastronomic haze, this view of mine was challenged.
In my search to justify my stance, I stumbled across this fabulous article by the Australian Business Traveler written helpfully 5 days ago (21 December 2015).
Essentially, travel cancellations due to severe weather or airline strikes; or due to natural disasters (that occur after the date your insurance commences) you are covered by insurance – everything else is up to the airline to compensate, reimburse and/or find alternative arrangements, and this could be over a number of days.
Kiwi Roamer, the less intrepid traveler 