This whole debate comes down to one's attitude to risk and how to manage it. The name of the game is to always have an escape route.
I happily fly SE over water, hundreds of miles on occassions, because I carry a raft. Sure, it may be defective and may not open and then I will die, but that would presume a failure of two unconnected systems (the engine and the raft) which is very unlikely - assuming the raft has been serviced and not been lent to some flying club where somebody tampered with it to see what is inside the package...
I don't fly at night, well not on a proper dark night, because there is no escape route. You will almost certainly hit something pretty hard. My night flying is either little bits getting home in the early evening, or whatever was needed for the UK night rating, the FAA PPL and the FAA CPL. I would dread doing the FAA ATPL in a SE (even if one could) since that requires 100hrs of night x/c.
I don't fly if the 0C level is below (or anywhere near) the MSA, unless the flight has guaranteed VMC all the way.
It's funny how many people cross the Channel without a raft (at least 95%, IMHO, including most school-sponsored fly-outs) yet most are happy to do a night flight.
Curiously, flying over mountains is something most won't do, but when you are up there over the Alps at FL160 you are usually totally spoilt for landing sites. Many large elevated flat spots are covered in thick snow, which is pretty good. No chance of recovery of the airframe but anybody should be able to land there. In practice one would aim for one of the valleys.