Sync errors will not clear, holds up all other syncing

I have an issue with syncing pictures from iphone as well as from my desktop. WHen i've made a collection and sync it, sometimes it gives me errors for one reason or another which make no sense as to whats actually happening. When this happens it halts all other syncing in the queue until the error is cleared. I attempt to clear the error and nothing happens. Maybe someone can shed some light on whats going on and how to fix it? I've attached screenshots to the sync dialog box and error.