Erika, I felt exactly the same way. There are so many to chose from and don't even get me started on the accessories. I went in looking for the biggest and best and tried not to have an anxiety attack over the prices and choices.
With the help of a friend, I decided to start off small. Where I wanted something that had all the bells and whistles to it, I finally decided to go with something small and simple.
The iPod shuffle is so easy to use. You have to have an itunes library set up on your computer and then you just plug one cord into your Shuffle and one into the computer and it does the work for you.
Look around at the different products that are out but try not to get too overwhelmed. It's easy to do with today's technology.
And when in doubt, don't be ashamed to ask the daughter for help. They will probably be more than happy to do so.