With all respect to your hypothesis, bpaggi, when push has come to shove and the dollars are on the table, very few will pay the kind of premium you are talking about for that last .017% of safety.
I flew for an exec charter operation with a mix of multi-engine IFR and singles.
Given the choice, the chairman for Toyota went cheap, so did the owner of Evergreen, just for example.
Funniest would be that the entourage would arrive in separate GIII's and Global Express for "safety" reasons, then all hop in the same 407.
malabo