Attachments have seemed to be difficult in a couple of ways for me.
Drag and Drop OUT of Wrike
1) When someone sends me an attachment that I need to email or save to my computer, I have to drag it first to the desktop and then I can load it into an email or drag it to the folder I wanted to save it in.
Drag and Drop straight from Outlook
2) When I want to upload a doc to a task that someone emailed to me, I can't drag the attachment straight from Outlook into Wrike. I have to drag it again, to the desktop first before I can add it in.
3) When I set up a new office and give them access to workflow projects that were created for them, I then have to go through and drag and drop attachments into the folder that I just created. It would be easier if we could select attachments to be duplicated as easily as custom fields, assignees, etc. Just a check mark box in the duplication options pane.