There's little to no evolutionary pressure towards the brain understanding how it functions.

Ok then, tell me where the evolutionary pressure came from for brains to consider and act upon things like burials, math, surgery, and brain surgery in particular.

Humans evolved for a long time before we understood anything about how our bodies work, so why would a brain have to understand itself to evolve?

Why should it?

Because it thinks. It takes in information and performs an analysis on that data. Surely over the time it would take to evolve, my brain thinks that it should understand that more than anything?

It understands how every other organ works in explicit detail at the the molecular level.

The only thing my brain can imagine, is that my consciousness is disconnected somewhat from my brain. It's as though my consciousness is inside a machine that it barely understands the workings thereof. Like a dog riding in a car.

1) Individual brains don't evolve, evolution happens to the gene blueprint by which embryos make brains, and it is fixed before the new brain has had a single thought;

2) Your brain definitely doesn't understand how every other organ works in explicit detail; controlling organs only requires being part of a good enough feedback loop to have the organ mostly function; your brain understands your heart "at the molecular level" about as much fruitflies do.

just because you're processing things doesn't mean you're processing what's required to understand conscious/intelligence.