I have found two popularly suggested ways to preform this task:
ogr2ogr - just take a shapefile and use ogr2ogr to put a shapefile in to a sql server database. This would work for a few shapefiles but is not a solution to importing LARGE amounts of shapefiles of many varieties.
Using QGIS, export into SQlite - I have had this one proposed to me a few times. Really this only adds the steps necessary to preform this to many many shapefiles.
And this third task I think may be the winner:
Exporting shapefiles into Postgis, PostgreSQL, then perform a batch database conversion from PostgreSQL into Microsoft SQL Server 2012 - After breaking down and buying software called FullConvert which claims to be able to connect the the PostgreSQL server and then copy tables into MS SQL Server in bulk.
The last method I think is the closest I have gotten to being able to preform this task. I'm going into the office tomorrow to preform this on the server locally because it fails every time I try to perform this task over OpenVPN.