OK, having read through this thread for awhile, I might as well chime in
with a few observations:

1) Roll the dice often enough, and they will eventually come up snake-eyes.
The question is whether they are likely to do that before something else
gets you. Most people want to make it more likely that they will die of
cancer or heart disease than in an airplane crash. Apparently we want to die
slowly and old.

2) Here in the Pacific Northwest, flying at night in the mountains is
dangerous, no question about it. Indeed, the mountain ranges around here are
possibly some of the most dangerous in the world. The trouble is, flying
anywhere around here at night as not much better. The whole area is
mountainous, heavily forested, with large tracts of water that is barely
above freezing year 'round. Visible emergency landing areas at night are few
and far between. Low ceilings, low freezing levels, haze, mountain
obscuration, micro-climates with weather wildly different from anything
forecast -- these are the norm around here. Many students around here manage
to log over an hour of actual IFR before they get their private certificate.
On top of that, the days get real short and real dark during the winter, so
restricting yourself to daytime flight is difficult.

3) Even if you live through an emergency landing at night in this area, the
odds of surviving until you are found are vanishingly small, especially
considering that most pilots do nothing to increase their chances of
survival. They fly without jackets or coats, take no survival gear, have no
way of signaling rescuers, etc. You are going to be wet and cold and
probably injured. Not good.

OK, if you want to die slowly and old, don't fly at night in the Pacific
Northwest, especially in the mountains. If you don't want to kill your son
or anybody else, don't take them with you when you fly little single engine
airplanes at night in the mountains around here. But even if you don't give
a rip about yourself or anybody else, I would ask you not to do it anyway.
Too many good people are killed every year trying to rescue selfish,
thoughtless bozos who thought they were invulnerable to the laws of
averages.