Poor query performance
This ended up being related to parameter sniffing. It just so happened that some oddly formed versions of this query were being executed RIGHT AFTER the stats were rebuilt. So the cached plan was not representative of the majority of the calls. I used the trick of copying the date parameters to local variables and this is working just fine, with little to no impact on performance. This doesn't answer why the histogram looks so "off", but it does explain my performance issues.