Box for Outlook - Allow Configurable Setting that will autocovert an attachment to a link when over a certain size
Sharefile's Outlook add-in allowed for you to define a size threshold for attachments. When that threshold was reached, it would automatically upload the attachments to Sharefile and then insert the link to the file(s)
This feature made it simple to share larger documents, or multiple documents that would cause bounce-back emails for trying to send an email with too large of size. This was also much quicker than taking the time to create a new folder, upload the documents, then attach the links for those documents to the email.
I understand that this would require some other types of decisions to be made, such as where does the file get uploaded to? Perhaps there is an autogenerated folder for each user account that it sticks the files in, similar to Box Reports, Box Shuttle Reports, My Box Notes, My Canvases, etc.
You can find some of their documentation here:
https://docs.sharefile.com/en-us/sharefile/sharefile-app/sharefile-for-outlook/change-defaults