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A little late, but you may also use the Datasheet view in SharePoint, right-click on the attachment cell and select Edit Attachments. From there, you can click on Add and select multiple files to load to the SharePoint List Item.


You start by setting default values to metadata, the default values for these 30 documents. Then, you upload them and you they have the right metadata. For the second question, you filter these documents and then you go to datasheet view. Then, you open an xls file and you fill the particular metadata in 30 cells. You copy them (ctrl-c), you go to the ...


You can't do this OOTB and worse if any metadata is mandatory then the files will remain checked out and invisible to other users as there is no initial version. However you can do this by script https://spfileupload.codeplex.com/ Other 3rd party tools may be offered - just Google - sharepoint upload multiple documents with metadata


The accepted answer here may work but it is not proper user of the API. The two main problems with this kind of approach are (a) exceptions are being thrown around for common cases (e.g. a folder that may not exist, actually doesn't) and (b) you often won't be able to give fine grained explanations to the user about why the operation failed because most of ...

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