ie would a pilot choose an option which carried higher risk because the chute was there as backup.
Of course it does. I'd fly a Cirrus over the mountains and desert of California at night, but I would not take a 30 year old Tomahawk on the same flight. The Cirrus is a step down from a twin, in that you have a backup if an engine fails over hostile terrain or at night and so therefore can be used as a real go places plane by the family.
I have done some flights in the past, i.e. Phoenix to LA at 2am in a clapped out Archer which I'd think twice about now I have much more experience, but would do in a Twin or something with a BRS.
Regarding "piloting skills"...I recall many VMC into IMC accidents in non cirrus types...