Great post!

I haven't read it but qualitatively, it rings true to me.

I think feeling like you are on the bloody edge of your own compentence is a
feeling we've all had and one that most of us seek out. It's the definition
of challenge. Having some fear and being cautious is healthy I think

Regarding leaky brakes and shocks and pushing the envelope.

Pilots I look up to don't fly with a bad brakes. They get it fixed. There
will be enough instances where you *discover* you have a bad brake and have
to exercise those "land in the first 1,000" skills. No need to knowingly
fly into such a situation. Ditto with the shocks.

It seems the longer you fly you either:

1) get more cautious and take fewer risks because you know things will go
wrong anyway and you need all the help you can get to overcome them

or

2) get more complacent and take more risks because you know things will go
wrong anyway but you can usually overcome them.

The trip with the xwinds, shocks, brakes, and passenger is one of those
situations where you are "picking up the package by its string".

....As in a passage from Flying Magazine many years ago. Some 'ol sage, when
asked what the secret was to a long, safe flying life, said,

"Avoid the terrain, don't run out of fuel, and don't pickup a package by
its string"

I always liked that one. It does require awareness that packages were once
bundled up with string rather than tape.