Flying is full of "what ifs." Some are easier to dismiss than others.
I'm the biggest pussy of them all... VFR/daytime only now, and I am just fine with that. LIke many have said in this post already, they
used to do it. I have done it too. Got my ass kicked pretty hard one night in some clear air mechanical turbulence over the coast range on the south coast of CA, I'm just thankful I didn't have my wife or anyone with me whom I wish to enjoy the experience.
I certainly appreciate the skill and mental fortitude required to take on additional risk, but we all fit the flying risk package into our lives differently. Nothing wrong with any of our choices. It's all perspective. For some, climbing into an airplane at all is a really big deal. At the other end of the spectrum you have Gump falling asleep at the wheel alone in a 207 at night in IMC over AK mountains, anus totally relaxed.
It's just how you look at it I suppose. I fly over the east side of downtown Portland all the time at 2000 AGL. I would have nowhere to go besides a residential city block if the prop stopped, and I'd be faced with the additional responsibility of not injuring people on the ground.
Good conversation. Just because many of us have resolved one way or the other on the topic doesn't mean it's not worth talking about. Feelings.