In my very humble opinion, I would take a Caravan over a Chieftan any day of the week.
Why?
What is the stall speed of a caravan vs Vmca of a PA31?
I'd much rather mush it into the trees at 50 knots than end up inverted and going down quick at im guessing over 75. It a matter of energy and inertia.
Plus with all GOOD Vans, there is a terrain page for when you are gliding in IMC. But if you arent keeping yourself updated on a map as to where appropriate low ground is then there aint no helping you anyway
j3