Reid is ready to drop in new and improved mark-up bar icons. I'm going to hand off a first pass at them. However, there are still a number of visual design issues to iron out, which I propose we do in parallel with development, since I believe all of the open issues have to do with visual design, not behavior.

The proposal is as follows:

Change the Email icon for the Communications Stamp to something more generic: e.g. a Person, in an effort to make clear to the user that "Email" in Chandler takes a back seat to the "Information Item" the user interacts with.

Change the Calendar icon to a Clock for 2 reasons:

Visual consistency The calendar is very busy and consists of many parts. Heikki has also commented that it looks like a calculator ;o) A clock is much simpler and works much better at small sizes (e.g. Sidebar, Summary Table, Mark-up bar)
Semantic consistency The other stamping buttons are about what you Add to the item to place it in a different context: (e.g. Addressing fields for Communication the item. A checkmark for designating the Information Item as a Task.) The calendar is the only icon that is about where you put the Information Item (on the Calendar), not what you add to it in order to get it on the Calendar (date/time metadata).

I've mocked up both the Calendar and the Clock for comparison. (Go to wiki page for images)

Tooltips

Send item? Address item? Can we say Send event? if we know it's also an Event?
Remove addressing fields (works for both Inbound and Outbound communications)

Add to Task list
Remove from Task list

Add to Calendar
Remove from Calendar

Never share this item
Allow this item to be shared

I've also decided to go with the oblong lozenges because while I agree that the circles are pretty, the oblong lozenges create a natural horizontal division between the Mark-up bar and the Detail View, whereas the circles create a repetitive up-down wave pattern that distracts the eye.

Things we're not addressing in this first round of Mark-up bar improvements

Communications status

In versus Out
Read versus Unread
Draft versus Queued versus Sent
1st time Send/Receipt versus Update

Sub-Kinds (Different flavors of Communications, Tasks and Events)

Mimi

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[Design] [Proposal] Mark-up bar button visual treatments

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