[abeppu]

I like this as a concept. The tricky part is now there are two audiences that the system has to avoid alienating -- it has to seem friendly and not creepy to the recipient, and it has to be harmless and non-embarrassing from the perspective of the 'sender'.

[lyricalpolymath]

Well, I imagine it's some kind of app that you allow to post on your behalf. When you allow it, you know what it will post. If you really want to go the extra mile you could ask each new member to tick off which messages they don't feel comfortable sending out before authorizing the app. But I think that is unnecessary or release 2.0 Moreover if you relate back to the group, the person can see the larger scope and, maybe, join on the effort.

I'd be more concerned that you get hacked like buffer did a few days ago and you start sending bad tweets as the members :) but besides that I'd be willing to "donate" a few of my tweets to this do-good project

[jbl]

It could also be as simple as the bot selecting a feel better buddy from a circular queue and asking that person to send a nice tweet to someone who needs it. This could either be "handwritten" or via some web app that authenticates on Twitter and lets you manually send a canned tweet (not unlike a share button)

[lyricalpolymath]

Yes that would be a solution too. But I think it increases the barrier to action and participation of the members of the group. I don't use that much Twitter so I would probably miss on the request for help.

I think the automatic bot style is the way to go. The importance is not the "really thought out message" that someone can send, while rather the low latency, the immediacy of the reply to those that need it. So timing is more important. At least this is what I felt from the positive comments you showed off in your blog post. :)