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.

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    Could you clarify why ogr2ogr is no option? One would think - since it's scriptable - that it would lend itself to importing large amounts of shapefiles. – underdark Oct 4 '14 at 7:59
  • I'm still looking into how to do that actually, like if anybody has all ready scripted a method to make this work effectively with a large volume of files that would be great. – Alex M Connelly Oct 11 '14 at 1:29
  • @underdark - ogr2ogr does not support MSSQL bulk importing. It uses regular inserts. For that reason, it is very slow. When I did this, I was forced to make my own bulk geometry importer using C#. It would be nice if ogr2ogr could take advantage of MSSQL bulk importing some day. – Damien Mar 22 '15 at 22:55
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    thanks for the feedback everyone, we found a SHP2SQL loader in an exe that enabled us to easily choose projection, file name, and data base destination and boom, uploaded. Wish the MS SQL data loader included this by default. – Alex M Connelly May 6 '16 at 17:17