i love this idea, i have always been into making tapes4 the soul
it is something I have wondered about, but it will be impossible to fit everybody's needs and satisfy any listener. You should put your own heart into it and make the best out of the idea. Collect what you and your friends love to listen to when you are together. Songs from the past bring up good memories, so just go with what you love and value and you will make yourself happy and most important, the people close to you, the friends who stuck with you when the times were rough, but you smiled and sang along...Does this help?..I hope so. :)
If you are traveling with children, the WeeSing "America" is wonderful!