In Outlook 365 for Windows there are alternatives to the usual ‘upload then link’ option for sharing large files via email. The principles are the same but the whole task can be done inside Outlook.
Insert | Attach File has a pull-down list of recently used files.
If the file is in a OneDrive folder, you’ll be given the option to either attach the file or share a link to the cloud saved version. This is more appropriate for sharing documents.
If you try to attach a file or video that’s too large, Outlook will warn you.
For any attachment, there’s an Upload option to save the file to a OneDrive account linked to that computer.
Choose the OneDrive account then wait while the file is uploaded.
Then pull-down the menu again to choose ‘Anyone can Edit’ or ‘Anyone can View’ (read only).
This option uploads the file to an ‘Email attachments’ folder. Choose ‘Open File Location’.