Something I do for my wife on occasion is burn CDs. Specifically, I download episodes of Dr. Joy Brown's radio show from iTunes and, when I get enough of them and I actually remember to do it, burn them to CDs she can play in the car.
I suppose I could download the shows any number of ways. The main reason for using iTunes is that I can easily take a group of MP3 and say "burn to CD," it realizes that there isn't any possible way for 24 "hours" of Dr. Joy can't possibly fit on one CD (by the way, after you strip out all the commercials, a "radio hour" is about 36 minutes), and it offers to burn the playlist across multiple CDs. I simply label the CDs using a Sharpie, stack them up, and feed them to my MacBook as necessary. The whole process takes about 6 minutes per CD and aside from prepping the CDs and the playlist, the process is fairly automatic.
Of course, the whole reason for going through these machinations is that the wife prefers the low-tech solution, or rather the high-tech solutions aren't smart enough to cope with things like the car turning off or even switching cars. The CD players in the car will remember where they were when you last turned on the car. Burning CDs is cheap and cheerful, albeit wasteful since the CDs are listened to once and tossed. I suppose it's a good thing I buy them at Costco where they are dirt cheap.