Can you customize what folder MAIL goes to when adding attachments?

Question

Can you customize what folder MAIL goes to when adding attachments?
My friend has 2 email addresses for businesses.
He has invoices in folders for both, and wants to set up the Mac like this:
When he writes from one email address and attaches documents - he want the Mac always to go to the corresponding folder for that company of his. Same for the other email address...
Make sense?
Can this be done?
Thanks in advance....

Answer 1

Please read this whole message before doing anything.
This procedure is a diagnostic test. It’s unlikely to solve your problem. Don’t be disappointed when you find that nothing has changed after you complete it.
The purpose of the test is to determine whether your problem is caused by third-party system modifications that load automatically at startup or login. 
Disconnect all wired peripherals except those needed for the test, and remove all aftermarket expansion cards. Boot in safe mode* and log in to the account with the problem. The instructions provided by Apple are as follows:
Shut down your computer, wait 30 seconds, and then hold down the shift key while pressing the power button.
When you see the gray Apple logo, release the shift key.
If you are prompted to log in, type your password, and then hold down the shift key again as you click  Log in.
*Note: If FileVault is enabled under OS X 10.7 or later, or if a firmware password is set, or if the boot volume is a software RAID, you can’t boot in safe mode. Safe mode is much slower to boot and run than normal, and some things won’t work at all, including wireless networking on certain Macs.  The next normal boot may also be somewhat slow.
The login screen appears even if you usually log in automatically. You must know your login password in order to log in. If you’ve forgotten the password, you will need to reset it before you begin. Test while in safe mode. Same problem? After testing, reboot as usual (i.e., not in safe mode) and verify that you still have the problem. Post the results of the test.