HI @Neil Hayek, I hope you're well.
There is a (confirmed) bug in Salesforce Files Connect: if you try to use the email component from Salesforce (which I think is a great feature), and attach a file from, say, a Files Connect-ed Google Drive, all seems to work seamlessly, except that, in fact, the attachment, is neither attached nor, of course, sent.
I think it's a big user experience problem, because everything works fine, except in this case which should also fine AND fails silently. To circumvent this, you have to remember to EACH TIME download the file from GDrive, upload it to Salesforce, attach it to the email, send the email, delete the file from Salesforce. If you do not delete it, there will be a huge number of duplicates (I cannot imagine a world where users look for the already stored Salesforce file and upload as a new version. This world does not exist), since everyone will need to download the file before using, to be sure they have the last version -something Files Connect links take care of for you-, waste a lot of space in Salesforce, etc.
I know for sure that this is not a priority, but can it become one? I think it's a great TTTC bug fix.
Thanks.