Need advice on an MP3 player/IPod purchase

Ok, ok, I know it's the 21st century but I have never had an MP3 player but I want to purchase one for my best friend and am not sure hwere to start. I did do some online research and the IPod nano looked pretty good but it appears that many are cheaper. Here's some background:

My friend loves music, downloads from bearshare and burns cds to listen to, but really only when she is in the car. Although I am sure she has many classics apparently a month old cd in her world is ancient so I don't think she needs huge storage.

She is quite active, can't sit still (someone who spins at 78 in a 33 1/3 world). She is always cleaning, weeding, ironing, cooking, walking the dogs or running errands so it would be nice to have something super portable.

One of her daughters got a media player and they couldn't figure out how to upload to it. She is not stupid by any means, but not extremely computer literate.

Sooooo, here are my questions:

1. How are songs aquired to you computer, are file sharing sites still in play?
2. How are songs uploaded from the computer, how complicated is it?
3. Knowing she is a music maven with the musical attention span of a gnat would you still recommend larger storage. Did you think you wold never use all you had and wish you had more?
4. Do some have other neat features that may be handy?

Any recommendations and/or experiences are appreciated. I guess ideally something very user friendly and portable. Cost is a consideration but she deserves the best, no matter.

Thanks in advance, DUers! I'll be in and out and check in as I can.

On edit: Also any recommendation on the best way/place to buy.

1. How are songs aquired to you computer, are file sharing sites still in play?
File Sharing is how most people do it.

2. How are songs uploaded from the computer, how complicated is it?
USB Cable that connects your Ipod to the computer. You go into ITunes and select which songs you want to add to your IPod.

3. Knowing she is a music maven with the musical attention span of a gnat would you still recommend larger storage. Did you think you wold never use all you had and wish you had more?
Depends on how many songs she has.

4. Do some have other neat features that may be handy?
Ipod has the shuffle feature which is really nice. It allows you to shuffle songs into random orders and play them from this list. Really nice, especially if you listen in you're car.

I assume that you can erase tunes and replace with new ones when you get tired of old ones. If that is the case I doubt she would ever need more than 500 tunes.

When you say you go into ITunes and select the songs to upload is that a program that comes with an IPod or do you just create a directory to store tunes in? If you purchase an IPod are you allowed free downloads from the ITunes site?