It definitely isn't going to be super easy; I would check into a service like Import.IO. Import.IO specializes in this type of stuff.
There is WDC connector to pipe Import.IO into Tableau as well.
Hope this helps!
First comment, yes what you are asking to do are outside the range of what Tableau supports. You are on your own to some degree.
That said, all states require public data, such as school information, to be publicity available to some degree depending on state and legislation. Student level data is verboten, but generally aggregated data like school district boundaries are almost always made available in the public realm.
Mapping data is it's own seperate aspect of public data. Publicly available mapping data is almost always made available in a format known as a Shapefile (which is actually a compressed file directory), generated for or by a tool used by cartographers know as ESRI ArcGIS.
School district mapping data for the US and governmental mapping data for most nations globally is easily found in this format via a search engine inquiry.
For example for Pittsburgh schools, this is the site that I found with a simple search:
And sure enough there is a shapefile for schools.
The next step is to convert the shapefile directory to a data file format Tableau can use. There are a couple of methods to choose from, described in these links:
Now, usually shapefiles describe polygons on a map, like the boundaries of a school district, zip codes, area codes, etc.. It appears this specific data only has points (Latitude, Longitude) for the center of the different districts. So, you can locate them with points, but if you are looking to map the actually district boundaries, you'll have to find a more detailed file elsewhere. (Hint, hint, you might be able to download here if you create an ArcGIS account online, http://www.arcgis.com/home/webmap/viewer.html?url=https://services1.arcgis.com/YZCmUqbcsUpOKfj7/ArcGIS/rest/services/PGH… )
If this helps you out, please give this response a 'like' or mark it as a correct answer so that others can find it quickly.
Tableau Online Deployment Advisor
PittsburgSchools.twbx 63.2 KB