Operating Systems make all of this much simpler by setting it up for you. Try to use only what they give you and you will go a lot farther with less effort. Buck the system and you're in for a world of hurt.
There's a better way to go about it. It's called: PAY FOR YOUR SOFTWARE. Then you might get support too. You want it for free, you bet your ass it's going to be painful to use.
By the way, I don't know who this Ryan Dahl guy is, but it strikes me as very naive to consider that groking the entire inner-workings of the complete organization of an operating system - from the development tools to make it to the execution and use of its applications - should somehow be simple for anyone. I wonder if he'd bitch that the kernel is hard to modify without affecting another component, or that different versions of software may not have been written to be completely backwards compatible with one another?
This is the real world. This shit is complicated because it evolved that way. It's almost infinitely flexible and powerful and gives you everything you need to do what you have to do - and you complain that it's complex? Grow up.