Truth to tell, though, my own experience is limited. I have my own tools that I've picked up over the years -- Audiograbber (a good medium-power tool) for ripping, Easy CD Creator (because it was there) for burning, a little iTunes for random online shopping. But those tools aren't all the easiest to use, especially for a non-techie like my mother. And I don't have much experience with the real MP3 players; I just have a CD player that handles MP3 discs.
So I'm looking for any and all opinions about tools for MP3s -- software for ripping, burning and downloading, and portable playback hardware. I'm much more interested in ease of use, rather than power -- odds are that I will set up defaults and my mother will never change them. Price isn't a major issue: while I'm not going to spend a thousand dollars here, I'm happy to spend a few hundred to get her the right equipment. What have y'all used, and what did you think of it?