Advice about Sharepoint collaboration with external users

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I have a customer who's relying more and more on Sharepoint to store files and share them with other users. It's construction, so there's a lot of drawings, big PDFs, that sort of thing.

I am sure there are people out there who have heard the complaints from users - why can't I send files, why do I have to send links, why is it so hard to upload stuff...can anyone suggest some tips or third-party tools that can help in these situations? Something that might just simplify overall Sharepoint usage for laypeople?
 
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