Hi sweets!
I started out with the second generation shuffle. It was the size of a cig lighter. It was the one that had the lanyard to wear around your neck. I loved it - it could fit in the strap of my bra with no problem!
I wanted to play it in my car and it wouldn't work with the cable I bought http://www.shopallmonster.com/mp3/
So I sold it to a coworker - (it help 120 songs) and upgraded to the 4 gig silver IPOD NANO. I LOVE IT!!! It plays in my car I use it more in the car than with the earphones. It holds I think 1000 songs. I paid $200 for it plus the extra warranty. I got mine at best buy. I found ipod skins on ebay got 3 for $10 to give it a more personalized look. I bought the JVC earbuds - they were like $20 - and they are very tinny. I plugged in the ipod ones and didn't change the volume and hit play and seriously the sound difference knocked me into the wall!!! I jumped back! I couldn't believe it! But I've heard that sony ones are really good tho.

The nano is easy to use once you get passed the initial startup. If you want a simple one - I'd go for the ipod shuffle 2nd generation - the one that clips - I think that is the coolest feature! I wish this one did that! But you can get a 'bigger and better' one for just a bit more money. My brother in law has a Zen I think and loves it. I bought my 10 year old nephew a cheap RCA model at Walmart for $35 for Christmas. It runs on AA batteries instead of recharging off the computer like the ipods. It held like 150 songs but the memory card someone bought my sister for her camera fit in it and so it held ???????? songs... he LOVES it. My sister got him an ipal to plug in and play off it.
My nano was acting weird the other nite so I got online and looked up the instructions and it said to reboot it so I followed the instructions and it's been acting fine.
The only thing that I struggled with - and still am - is downloading songs from other sites other than ITUNES. I am just not computer literate enough to figger it out. I have uploaded all the songs that I wanted from every CD I own to it plus several ITUNES songs and have less than 400 songs on it. Uploading CD's to it was really easy I thought. You just have to make sure you sync it and transfer the songs to your playlist. After I bought the shuffle I was like "I'll never buy a CD again unless I want the whole thing- most of my cd's are for one song - for .99 I can buy it off itunes - upload it to the ipod and still play it in my car." If I could figger out who to do it from the 'free sites' I'd be even better! lol
good luck and let us know what you find!