I feel your pain, I really do.
Luckily the iPod classic is the only iPod I feel is worth owning, due to its massive storage space, so I feel like I really lucked out there. But at the same time, I have trouble recommending MC to new users, or anyone looking for a "better" media player if they own newer iPods. The fact I have to actually warn them about the refusal (if I recall correctly) to support, after gushing about how great the program really (truly) is, it makes me feel bad in some way.
And I certainly warn people, because it appears that JRiver does not (I never noticed any overt warnings). I suppose it could be argued that with a program that has you purchase from inside itself, and that there is a demo available, users would be aware. But that doesn't mean someone wouldn't find out later if they got a newer iPod after only using an older supported generation.
I suppose it could be said, the majority of MC users might have players other than an iPod too, but it just rubs you the wrong way, when an application trying very hard to bill itself as the #1 Media Player / Library Manager doesn't even support the one of the most popular devices ever created, beyond a certain model.