Good points. This is the thing. This happens every season. He doesn't renew early, and he never, ever lets me know if he's returning or not, but he's usually not the last one in after we roll. Overall, he's an ok, albeit quiet owner. He's always been cooperative, and has never caused any controversy.
I wouldn't worry about it so much if my world had any openings that weren't "pre-accounted" for. Besides him, we only have the one confirmed opening (taken), and the rest have confirmed through trade chat or have reupped already. This one person could be holding up the whole world, and all the guy needs to do is simply return a trade chat or sitemail.
Am I asking too much?