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As part of my organisation's move to SharePoint, I have been given the task of setting up a SharePoint site for my team as well as migrating my team's shared network drive.

Luckily, the folder structure on the shared drive is already fairly well organised, and I have been able to write a Python script which uses the full file path to automatically associate metadata tags ("Contract", "Month", "Year", "Person", "Travel", "Budget"...) with each file.

My aim is to set up one SharePoint library for our team which will allow users to access information easily and quickly using metadata search, without having to navigate through a complicated folder hierarchy. Since I am new to SharePoint, my questions are

1) Is this approach feasible / recommended?

2) Assuming I have some form of structured text file whose entries are network share file paths and their associated metadata, what would be the best way to migrate these files to the SharePoint site automatically?

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I created a program like this for internal use, but it is fairly easy to do it, you can go either with PowerShell or CSOM or SSOM, CSOM allows for uploading from a non SP Server (do remember to install the SDK on the client (not on the server, it will break it)). The biggest issue you will have is converting the text to the actual value SharePoint expects (Managed Metadata and multi value columns might give you issues here). Probably you want to do it a I did, set up a seperate config file where you define your input file metadata columns and map them to the metadata in sharepoint, as well as specifying the field type (or retrieve it dynamically from SP). This way you can have some logic decide how to Set the SPField's value.

EDIT: Having prior knowledge of the SP API should allow you do it fairly generically in about a week's time.

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