I've listened to the Klipsch only in Apple Stores, which are chaotic, but that's one I'd certainly consider if I were faced with the choice of getting a home dock for myself (or my father-in-law!). Price, performance and looks seem pretty good.
I have a Logitech mm50 for traveling -- although it could be used around the home, as well. I use it in hotel rooms and guest rooms, and while not as bassy as the Klipsch, Bose, etc. units, it's very packable yet it can fill up a room loud enough that it can disturb anyone in a neighboring room. If he's going to be traveling or wants to use the built-in battery when outdoors, that's a real good buy, particularly in terms of versatility.
But for stay-at-home "oomph," the Klipsch would be good. (Then there's the brand-recognition factor of the Bose docks -- if he's the kind of person who assumes something's the best because he's heard of it, and you need to score points with him, then a Bose might be appropriate in such a case, if you want to pay that much. Of course, for the price of a Bose, you could get him a quite good mini stereo system that plays DVDs, CDs, CD-R's, etc., and just have him connect his player to that through the AUX in port.)