Old Akro, some good thinking there, you’re clearly showing your experience in this area.
To further discuss your point that I’ll call the “transition from VFR to VFR in IMC,” do you think that many of the pilots that have been lost in VFR to IMC accidents are capable of flying safely on instruments assuming all things are going well? As in, fly straight and level in IMC, climb and descend happily and navigate to a waypoint? I personally feel like the answer would be a clear yes….
Therefore as you’ve pointed out, I feel like the issue is with the transition to IFR (or in this case, a VFR pilot flying safely in IMC). As you say, you need to be prepared to fly in IMC, to think ahead, plan your altitudes etc, which I’m sure many VFR rated pilots could handle easily, however by preparing to do this early you KNOW that you are breaking the rules and you KNOW the better option is to turn back and land elsewhere as even IFsr pilots do sometimes. Leaving it too late to make the transition is where it all falls apart and happens quickly.
Not directly talking about this tragic crash, but in general… are we that afraid of the regular that we would rather kill ourselves and our passengers than fly deliberately into IMC? Seems like it.