Damn. I wish I had read this post more carefully before responding. You don't want to play one song so much as play a playlist stored according to the file storage system you've grown accustomed to. Am I right? You want to be able to play everything in the Oldies folder or go down a level and play only everything in the Folk folder, or go down another level and play only Simon & Garfunkel? And you don't want to have them loaded into iTunes because then it will play music you didn't want to hear that isn't folk as soon as it's done playing the oldies?
I ask because I think you're making things unnecessarily hard on yourself. Obviously if you're open-minded and patient enough to use a Mac even though you're used to Windows, you ought to take it one little step further and discover the wonder that is iTunes. With iTunes, you can group your songs all these different ways and play only the group of songs you want to hear, and you can do it very easily. My suggestion is that you adopt a new system for playing music. Have you clicked on the "Browse" eyeball at the top right of the iTunes window? It will let you limit what you play by Genre (Folk), Artist (Simon & Garfunkel), and even album (Concert in Central Park). And you can put all your Oldies in a playlist listed at the right by either manually highlighting and dragging songs over to the playlist or by creating a smart playlist that automatically includes everything in the Folk and Rock genres (or whatever genres you please) made before any year of your choosing. And on and on and on. The possibilities with Smart playlists are really quite breathtaking. I have only scratched the surface of what is possible with iTunes.
I have a friend who is a PC user and he recently got an iPod. I convinced him to use iTunes rather than MusicMatch. He slowly warmed to it. Then one day he was over at my house and I did something with iTunes on my Mac and he wanted to know what I had just done. I don't remember what I did, but it was something really simple that he wasn't aware of. I realized that he hadn't come remotely close to appreciating how many different ways he could sort and group and locate music using iTunes. He didn't know you could highlight many files and right click on them and use Get Info to edit the ID3 tags of multiple songs at once, which is very handy if you want to change their genre or add the Year, or correct the artist name, etc. He didn't know about using the Browse feature (and turn on browsing by genre in Preferences), smart playlists, sorting by columns, etc.
. It's almost the perfect app. If only I could turn off that feature where it adds songs to its master playlist when I open a file...
