Here's a screenshot of my incredibly simplistic process:
You'll notice that not only do I use a hierarchical structure, but I also still use XP and poor little WMP. I dunno... it plays my music when and how I want it to. I dunno if that's considered "settling" or not. Maybe my expectations are just abnormally low.
Anyway, I've been using this process for years without any issues.
I probably seem outdated and unrefined to most of you, but I'm a man of practicality and I pride myself on it. I know where everything is, and exactly how to use it. I don't lose things and I don't get errors. It just... works.
Anyway, that's me.