I believe very few pilots depart into challenging weather because of the chute.
On the other hand I do believe some pilots will fly at night or over terrain that doesnt offer good forced landing opportunities because of the chute. I am one. I have always found myself to be very uncomfortable in a SEP at night and although I have run up some hours I would no longer chose to fly at night in a SEP without a chute. With a chute it worries me a great deal less. I also sail, and perhaps because of that I have always been very uncomfortable flying long sea legs when I know the sea conditions are rough. The idea of landing into a 5 foot swell just doesnt appeal. With a chute it also worries me a great deal less.
However, I also believe that because the Cirrus is such a capable aircraft pilots are lulled into a false sense of security. In fact a Cirrus is not that capable. It is no more or less capable than most SEPs; the fact that it is faster and has gee wiz avionics is nothing to do with anything. Unfortunately pilots dont always realise that and think a Cirrus will "take it".
Of course a Cirrus does have some useful additional capabilities. It does have an abundance of power, which can be useful, it does offer the best situational awareness of anything in the class, when fitted with weather and radar if used properly they are life savers, and so is the green panic button. So Cirrus have done a great deal to provide some useful tools to keep you out of trouble, but I think that is the key they are there to keep you out of trouble. If you get into trouble the de-ice, anti-ice will put you in front of most SEPs as will of course the chute, but beyond that it is still a light single thats going to be thrown around just like any other light single.
I always recall my first trip in a twin in some rough weather. It was really unpleasant and I shall happily admit to be unnerved (is that a posh way of saying scared!). Hitting my head on the roof really hard a couple of times probably didnt help. Of course because it was a heavy twin I thought I could fly in anything. It was humbling to listen to the CATS arriving at Gatwick - yes they were working harder than usual, and yes I only heard one other light aircraft on air the whole flight, but it was humbling how well the CATS were taking it in their stride. There really isnt any substitute for size, is there.
