iTunes music organization and playback help

[xrayeyes]

So I've had a problem with the same 30 songs or so playing over and over even though I have "shuffle" option on. I did some more investigating and it seems my music library is sort of, well, messed up! So, when I have the shuffle option on and the song playing, it shows "1 of 30" instead of "1 of 157".

When I looked more closely at my sync options, all of my songs are listed as "Albums". I suspect it's because I have a mishmash of songs I've collected through copies, iTunes, YouTube, etc. So, many of my songs are named with the artist and title all as one. I think I tried renaming in the past but IIRC it didn't work.

One question I have is the media folder options in "Advanced". I have the option chosen to "Keep iTunes folder organized" (places files into album and artist folders....). I had thought I was suppost to have this option checked for optimal use, but now I am wondering if this is what has disorganized my music folder?

 

[xrayeyes]

Well, I just figured out one problem I had. I right clicked on the song and then "info" and it let me change the info, including the artist and song info. I had not realized it would let me change it there. Once I get done with all of that, I'll try resyncing everything I guess and see what happens...

 

[xrayeyes]

I renamed everything and also listed the song in the "sort" option of the info and now I have "1 of 36". Hoping someone can give me something else to look at???