Not sure if this already does this or not but supporting advance shapes such as Polygon with holes, MultiPolygons, MultiLinestring, & Geometry/Geography collections would be good. I wrote this article a while back that supports some of these complex shapes: http://rbrundritt.wordpress.com/2010/03/06/multipolygon-multilinestring-classes-for-bing-maps-silverlight/ Feel free to use this code in this project. I plan to release an updated version of this blog post in the next month or two which includes some optimizations I've made which make a big difference in performance. If you are interested I'd be up for helping integrate this into this project.
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