Challenges with Apple Mail auto-complete

Hi all,
I'm seeking advice regarding some challenges with Apple Mail auto-complete email addresses for a friend's AOL mail IMAP account. Main issue: in Apple Mail, recently contacted email addresses are not appearing via auto-complete. As such, I'm doing some research for him and have some questions:
- Any resources on how email contacts are managed in Apple Mail?
- Any resources on how email contacts are managed in Apple Contacts? What's the difference? I'm not 100% clear how they are linked.
- Seeking alternative to Apple Mail for someone who is legally blind. Are there some alternatives with a simpler interface and possibly better integration with VoiceOver? Just curious
Any help is appreciated.
Mac Mini (late 2012)
Mac OS X 10.8.5 (12F45)
Apple Mail v 6.6
Apple Contacts v7.1

1)  Reindex Mail
Go to your User's Library folder. (if you don't know how to find, see this link.)
http://www.needhelp4mac.com/2013/11/how-to-enable-users-library-folder/
Scroll to Mail folder.
Select the V2 > MailData folder.
Delete any files in MailData with envelope in the name. (should be 3)
When you open Mail it will re-index your files.
2)  Search is based off Spotlight cache files.
HOW TO RE-INDEX YOUR SPOTLIGHT CACHE FILES
From the Apple menu, choose System Preferences.
*  Click Spotlight.
*  Click the Privacy tab.
*  Drag your drive to the list. Wait a couple of minutes.
*  Remove the item you added.
*  Spotlight will re-index the contents of the item you initially dragged to the list.
Contacts in Mail
Under Window in the Menu bar, select Previous Recipients List. If the person is in your Contacts, there will be an icon next to the email address. You can add entries to contacts or remove from the list. For example your friend got a new email address but autofil wants to use an old email address. Remove the old entry.
While Mail and Contacts are two separate applications they are tightly integrated.
I'm sorry but I have no other suggestions for a better email client.
Download and run the Mountain Lion combo to refresh your system files.
OS X Mountain Lion Update v10.8.5 (Combo) 831.81 MB
http://support.apple.com/kb/DL1676
Hope this helps!

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