When was the last time you listened to a Nano?
I personally don't think it's quite as bad as most people think it is, I own both a Cowon D2 and just about every generation Nano released. The 5th gen Nano is a nice dap. The radio, video, pedometer and other functions etc are great additions over the 4th gen.
Teamed up with some decent IEM's it's a good package, the user interface is in my opinion easier to use that the D2's, the Nano is all together a nice slick all-round package. The build quality is in one word, superb.
You know I've just picked up a copy of What Hi-Fi's Ultimate Guide to Technology for 2010. The best DAP in thier opinion sub £280 - The 16gb iPod Nano. The best DAP in their opinion over £280 - the 64gb iPod Touch. Other UK gadget Magazines also highly rate the Nano giving it the top marks (Stuff and T3 for example).
They can't all be wrong or biased, Apple products seems to get a really time here on Head-Fi, with everyone bashing there products, even the one's not released yet (iPad).
Call me a Fan-Boy if you wish (I probably am), but personally I think your father would find the Nano a lot easier to use and live with than anything else out there.
Chuck the white Apple Buds away, get him a pair of Senn CX-300-II's as a minimum and I'm sure he'll be over the moon.