This situation begs a Low Altitude IFR route structure with a GPS Approach at each end using the latest technology, with automated weather reporting at each end.
Add modern lighting aids and equip and train for SPIFR operations and I would see safety be very much improved.
What is going to be done today is not that much different than back in the 1980's....when it was a two pilot S-61 doing the job.
Let's think back to some notable crashes that give us a hint at the pitfalls of doing a VFR flight in marginal VMC conditions...day and night.
One thing that does argue for a new way of doing things is that the Pilots flying this operation would become very familiar with the Approaches at each end if they did them every time...every flight...every day..
If those approaches and missed approach procedures were pre-programmed....and the FD and Autopilot was working and flying those approaches.....combined with the other required equipment.....why would it be a problem for a single Pilot to fly the flight?
The fuel requirement for an IFR Diversion would the largest hurtle.
The revenue provided by additional flights in marginal weather should begin to pay for the extra costs I am thinking but it would take a detailed study to make that determination.
My personal opinion is it should be Two Pilot crew.....as I am old fashioned and learned the hard way that all that fancy Gucci Kit doesn't not always work and when it doesn't the workload on a single Pilot ramps up very quickly.