djlexey,

Either way is good although we recommend using crates if your using an external HD simply because when you add iTunes in the mix things can get complicated.
I on the other hand don't use an external and I do use iTunes to organize my tracks.
It comes down to getting to know either or both programs.
In iTunes you are able to download track information which does save a lot of time but using crates is less complicated because you won't need to get to know iTunes.
Your going to have to spend time either getting to know iTunes better or writing in your track information manually.

I don't quite understand this question?

about the iTunes.... when you have a file in iTunes and you go to "show song file" it is organized in your iTunes folder under atist/album/song name.... so then when you transfer your entire iTunes library it is organized that way... by artist rather than playlist. So what I want to do is say... take my "reggae" playlist. And be able to drag it like a folder with all the tracks inside it to my external hard drive. Possible?

Are you trying to move all your songs to an external drive but still want them to be organized the same way?

If so all you need to do is copy your entire iTunes music folder onto your external HD (keeping your XML and iTunes library files on your internal HD) and go to the preferences\ advanced\ and change your iTunes music folder location to read from your external HD.

I want to import etire crates into SSL from folders labeled with those crate names. Like take a folder called 80's and import the entire folder into SSL to a crate called 80's. So now I need to have all my 80's music in that folder that I am importing. I don't want to use iTunes with SSL so that is why I am importing all the files/crates. So I am trying to figure out if there is an easier way to create that folder with all my music in it without having to open up each individual artist from my iTunes folder and drag that individual song to an 80's folder.

Basically I want my iTunes playlist "80's" to be an actual folder. Does that make sense? If you go to music/iTunes... it is organized by artist name. I want it organized by playlist.

Yes, if your just trying to use crates all you need to do is copy for example, all your 80's tracks into an 80's folder and then import those songs into an 80's crate inside SSL.
If your taking those organized folders from iTunes you will still need to open them up to drag them into crates inside SSL.