The issue with this operation is whether the crews come under pressure from the ticket seller to fly when they shouldn't.
It's called "Commercial Pressure" and it doesn't necessarily exist between a paper airline and an aircraft operator, during my airline career I worked for some 11 aircraft operators and, whilst illegal, commercial pressure is pretty much commonplace.
Often it will be from the commercial department, after all their primary concern is to sell flights with bums on seats, and often they don't like to hear of operational problems such as a kaput weather radar and en-route thunderstorms and the fact that the commercial department, in this instance, may be merely a ticket seller doesn't change that it is commercial putting pressure upon the crew and particularly with regards to exercising commander's discretion.
That said, and particularly in this day and age whereas an increased degree of commercial decision making has been placed upon the aircraft commander, in lieu of professional trained and qualified staff in an operations/dispatch department, often commercial pressure is self inflicted by the crew member(s) when, perhaps, they may see writing on the wall whilst they need to feed their spouse and kids, pay the mortgage etc.
The point here is not to blame it upon a paper airline scenario, commercial pressure is commonplace and if it does exist in Citywing then it is not unique to their style of operation.