You're on a very slippery slope. Throw the iPod in the garbage. NOW.
I started innocently enought with an iPod for the son. After discovering that iTunes sucks on Windows I was somehow convinced that my daughter needed her own iPod and boom a Video Nano enters the picture. iTunes still sucks on a PC (crash/lockup if you even look at it) so the next thing I know I have a Mac
The cassette adapter is totally dependent on how good your factory cassette player is. Apparently a Land Rover tape player sucks cause the adapter I bought lasted ~ 90 minutes and is lying (melting) on the I-15 East of Yermo. Have not tried a FM transmitter deal cause I know it will suck too. So now the only option is to delete the CD and go with a hard wire or spring for a entirely new (non stock) sound system.
Just burn CDs and get on with your life.