There are a few things which (to me) seem bad risk management
- night flight, in a single
- flight over terrain (especially mountains) shrouded in cloud, in a single
- flight in icing conditions, with the cloudbase below the MSA, in anything but a seriously de-iced plane
- flight over dense forest
The first one has to be done occassionally, and almost everybody has to do it to get certain licenses. The 2nd one and the 4th one are comparable; perhaps OK to do very occassionally (well, I've done it...). The third is a real problem. The 4th...??... you just have to get on with it and keep fingers crossed.
But there is a lot of double standards.
A lot of people fly at night in a SEP, but would not fly over water. A lot of people fly over the Channel without a life raft (pretty much the norm to do that on the school/club scene as far as I can tell) but would not fly at night. Etc.
I still have to do the FAA CPL night flight, about 300nm......