Some are prepared to do it others are not, the aircraft does not know it is in cloud or night etc.
I agree completely, the airplane does not know but having an IQ above an inanimate machine I know where I am and not wanting to play Russian Roulette with an airplane I don't fly single engine at night, in IMC or over water.
Met another ferry pilot a few years ago in the parking area of the airport in Luxor who was delivering a Cessna 172 from the USA to somewhere in the sand box. We got talking and I asked him how he felt in that thing during the North Atlantic crossing and he said the same thing, he felt no fear because the airplane did not know it was over water.
That mindset is something I can't understand.