Looking for a way to organize correspondence

I’d like to do a better job of tracking correspondence. Your thoughts greatly appreciated.

Right now, I’m thinking I should make a group for each correspondence tree. A letter I mailmerge out to 100 members of Congress gets a tag for each recipient. For instance, there would be tags for Senators Larry, Moe, and Curly Howard for a letter mail-merged to them.

When the Right Honorable Senator Moe Howard replies, I tag it with Moe Howard/original topic/yy-mm-dd.

That way, if I double click on the Moe Howard tag, I focus on the letters I’ve sent and his thoughtful replies sorted by conversation.

Replies to Mr. Howard’s replies get further subtagging. That way I can follow the conversation.

I’d like to track the slackers who don’t reply, too. I think I can do that with exporting a metadata overview for exploration with one of my other favorite tools, Easy Data Transform.
Contacts Journal CRM in the App Store looks nice. I’m suspicious of nice looking tools for narrowly focused tasks, though.

Better to stick with the One Ring to Rule Them All, by which I mean Devonthink.

Any ideas?

I’ve automated my email capture (in and out) with applescript
(a version of the script provided by Devonthink)

The script could also automate the group creation and tagging

Seems like a lot of tags
I think I’d just use names; topic and dates are stored in other metadata

Good points, DTLow.

I archive my email in DT where I hope someday I can actually plow through it. For this use case, I want to organize letters, photos, spreadsheets, and other file types relating to correspondence, too.

You’re right about the date.

What I want to achieve is I’d like to look at a tag for a letter I sent. The “reveal tag” function would take me to the correspondence chain with any particular recipient of the original letter where I could navigate the conversation and reference other people.

Speaking of email archive, I set my import preferences to group by conversation. I also like to clean up by chronological order, so I make smart groups that search inboxes for any document. I see I also have “kind is not group,” but that’s probably redundant.

The sort order is set to date created, so I get to have my conversation groups and chronological order, too.

So far, that’s working for me.