I don't know the solution to your problem but my 'get around' way would be to create a shortcut and have it on your desktop. That would minimise a bit of the tracing through the file system.
As for putting attachments to emails, using either Thunderbird or OE, I just click and drag the required file across, having opened the file - saves a lot of effort and time.
I don't know if that will help you just now but it' a thought.
Again, sorry it's no help to the actual reason for your problem happening.