Update #5 I guess it\'s bounty time. 100+ views and no one\'s taken a stab, even with the code sample I\'ve posted. How about some reputation points!

I created a project based on your CalloutMapAnnotationView demonstrating a IB based solution. Arrow keys animate motion of the location annotation and it's callout annotation. The callout now also automatically resizes based on the supplied contentView, and the view is loaded from a separate nib. Good luck!
https://github.com/jacobjennings/JJMapCallout