I would pay $50 for an app that replace both Apple Mail and Address 
Book/Contacts if it could do the following:

I'm looking for a Email/Gmail client that *really* understands gmail 
labels, and has a tighter interface to the address book, or it's own 
address book.

Here's my dilemma:  I've got 6000 contacts, including my 'other' bunch.  
These are split between forums, friends, and business.  Conversations are 
labeled in Gmail.  But this information is not reflected in contact groups.

*A:  I want 'smart contact groups' *
    If I can filter on it, I want to be able to make a group for it, or 
pull a list of addresses from it.  E.g.  label:lilacs after:1-Jan-2012
   I want to make a  group that I've not had contact with for N 
days/months/years.  
   I want to have a group of all people who participated in a conversation 
where at least one message was labeled "Lilacs"
   Show me all contacts with addresses in the From: To: or CC: fields in 
messages with Subject:[Lilacs]

*B:  I want a way to show all conversations (threaded messages) that this 
address participated in either as From: or To:* *but optionally ignore BCC 
and CC.*

Lots of these contacts are email address only.  They are especially hard.  
But even with a name, it's difficult.  I want an address book that allows 
me to edit the card, and view the relevant email at the same time.  Looking 
at the address I've usually no clue who it is.


To do this in Gmail contacts, I have to:

Mouse over the contact in the list
Pause while the summary card shows up.
Click on show recent eails.
Possibly open one or more emails to figure out what/who this person is.
Try to find out what addtional information I can extract (name, phone,)
Keep all of this in my head, or do a bunch cut and paste to a separate 
window.
Go back to contacts.
Find the address again.
Edit the card
Assign the card to one or more group lists.
After:  Since I have a three screen setup, I run one browser window with 
Contacts, and one with email, doing a search for each contact in the mail 
window.  More efficient than above, but it takes two monitors.  *C: I want 
an address book that shows what groups the contact is a member of.*

*D: I want an address book that show what labels have been applied to this 
person's messages.  *

My notion here is that the line between labels and groups gets blurred. 
 Labels can be used as source info for smart groups.  Addresses are one of 
the possible results for doing a search on messages.  E.g. The default of a 
search may be "show messages"  But I want the option of a search to be 
"show addresses"


***
*E:  I want the ability to 'relabel' so that if a label applies to one 
message in a conversation, it applies to all of them.*Labels apply to 
messages, not conversations. 

*F: I also want to be able to sort  and filter messages and contacts by 
things other than first or last name.  *Show me members of group foo who 
I've had no contact with in the last year.  Sort the members of group bar 
by the number of emails they have written to me.   Find me addresses of 
people I've emailed three times since their last email to me. 

*G:  I want smart merge*

One program I trialed lost all list information when you merged two 
contacts.  I want it to be smart enough to do the right thing most of the 
time, based on timestamps.

*H:  I want to add people to certain lists on the basis of filters run on 
incoming mail.*

*I:  I'd like the program to be smart enough to be taught patterns.  *

E.g. A kiiji response is in a certain format.  If there is a name, it is 
likely on the last line of the quoted response made on the kiiji web site. 
 I'd like it to be smart enough to spot things like, "My number is 780 555 
1212"  or Call me at…    

This intelligence needs to be able to cough up the snippet on demand.  So 
that I can see it in context.

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