try cowon for classical music
I have used lots of different mp3 ripping software for my classical CD's and have settled on Media Monkey. It has More features than most other Media player software
As for portable MP3 players for classical music, I recommend anything from Cowon, which generally gets the best reviews for sound quality.
I have the I7, which is now being replaced by the Cowon Iaudio 9 (available in 8gb, 16 gb) on Amazon.
A big advantage of the Cowon players is that you can use file/folder browsing. I have never had luck with tag browsing with classical music, where order of play is important. All you do is plug in the player and drag folders from your computer to the player.
You also may want to consider the the Cowon IAudio S9. It has the same features as the 9, but has a bigger display for video.