I have suggested to Pipedrive that they make it possible to select a file already on the Deal, when sending an email. So you don't have to download it and then upload again. Do you think that would be useful?
100% It is very cumbersome to first download a file from pipedrive then attach it to an email to send it. This should be very high priority. Maybe there is some technical aspect of the development environment that is preventing this? I actually switched from using Safari to Chrome bause Chrome put the downloaded attachments in the footer of the browser which made it easier to grab and drag to an email. Safari put them in a folder on my computer.