I'm in much the same boat, my path to get where I am, was meandering and long.

I've worked with developers who fully understand the systems they are deploying on, and developers who develop for an abstraction of services rather than a real world environment - I tend to prefer the former to the later because the deployment process is much less taxing, even though the later tend to have better luck moving their software to another platform in the future.

But I'll echo you, every time I've learned something hard, it's because I got way out of my depth and had to learn how to swim all over again.