How could you create 'Last Time Contacted' Smart Mailbox in Mail app Lion?

Hello!
For the purposes of maintaining regular contact with a large group of contacts in your address book:
How could you create a smart mailbox in the Mail App (Lion) which contained that last unique sent/received email from each individual contact?
So ideally just the last email per contact. For my purposes I would then sort by date and find the contacts I havent emailed in a while and re-initiate conversation.
I also thought that perhaps it would be possible through Automator? (I am not very familiar with how to use this app)
Any ideas/solutions would be very appreciated!
nmarks
(running lion 10.7.4 macbook pro late 2011)

Okay, I think I just discoverd a workaround. This will work if you're lucky enough to already have a smart-mailbox folder that persists after close. (Somehow I had two such folders that already existed and weren't subject to the mysterious disappearances on closing the app; perhaps I created them in a previous OS X release?) Anyway, here goes:
Locate an already existing smart mailbox folder that's working properly. Select the folder (in the sidebar).
Duplicate that folder using the "Duplicate Smart Mailbox" Command. (It's on the contextual pop-up menu or available via the gear icon in the lower left of the window). This should produce and exact copy of the folder and the boxes inside, appearing at the bottom of the smart mailbox list.
Edit the duplicate folder to put the smart mailboxes you want in it, and delete the previous mailboxes (duplicates) that you don't want.
The new folder structure should now persist between launches of the app.
There you go. Not the most elegant process, but workable. Don't know if there's a method if you don't have at least one smart mailbox folder already though.

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How could you create 'Last Time Contacted' Smart Mailbox in Mail app Lion?

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