Re: I am looking for ...
I have an older 160GB iPod Classic. I use it for both audiobooks and for music that can either be listened to when driving or when I go out for my torture sessions...em...err...I mean my walks up and down the road.
Although I have my issues with Apple, as they seem to make things harder than they need be to do the simplest things, this was the largest HDD capacity available when I bought my MP3 player, and it still seems to be at first glance today.
For good or for bad, you use iTunes as your central hub for installing media on the unit, so once you learn how to navigate that program it's all rather simplistic if you don't tax the program too much.
As for headphones, I've always preferred Turtle Beach products (mostly for gaming), albeit they are on the pricey side (but don't you get what you pay for?) but I also use a set of over-the-ear JVC wired headphones for my use when superior sound isn't important.
Both of these were purchased at Walmart over the years. Whether they still stock them, or they are even made today, I have no idea.