It gets especially bad once you add multiple iDevices and use them for the same purpose over different time spans.
Example: If I get home and want to continue listening to the current podcast on the iPad, I have to first sync my iPhone and then the iPad.
And if, on the next day, I want to finish the podcast on the iPhone, I have to remember to sync both devices again (iPad first) or I'll have to use the awful time slider on the iPhone to find the correct play position again.
Same goes for Audiobooks where it's even worse due to their length and sometimes more monotonous content (makes it harder to find the correct play position, or might spoil the content if you are really unlucky and skip ahead too far).
And don't get me started about the fact that at least my iTunes install insists on either installing all new iPhone-apps on my iPad or deleting all apps I installed directly from the App Store on the device, depending on how the checkbox is set.
This ugly mess has to end.
It worked "ok" (wireless podcast sync would always have been nice) while we had only one device. It became totally broken once we had multiple devices.
Yeah - what a luxury issue to have, but it's still totally non-apple and doesn't at all match their usually very slick user experience.