If that is the case, then I would definitely go with Sony. They are tough. I had my original one for 4 years before it kicked the bucket. Still the only thing to consider is how much music they would want to put on it. A regular $40 Sony MP3 player can fit about 800 songs. That is what I got with it.
The Sony supports everything from games to Podcasts. You can watch movies, episodes, basically whatever you want. The only thing, again, would be the space. You would get far less space should you put movies and such on it. Unless you go for a higher end one. The one that was released not so long ago to places like Best Buy was a touch screen around $400. Had plenty of space.
As I said in my previous post, Sony works with Windows Media Player. It is a simple drag-and-drop function. You have items in your playlist or library, and you simply drag it to the Sync tab. When you have everything you want, you click Sync and it all goes there.
I will point out that Zune, although Microsoft developed, does NOT work with Media Player. It has it's own software akin to iTunes.
Plus, if you buy from a place like Best Buy (who carries Sony and iPod), you can buy a service plan that protects the product. So as iPod has Applecare, that does not mean everything else doesn't. Just make sure you buy from who you want to buy from.
Overall, I highly recommend Sony based on what you are looking for. Both of you.