Well, I think he should go to each funeral. After all, the man's got nothing better to do. Seriously, we could bog him down in the sad facts of death and take him away from the pursuit of victory. Ultimately, we'll lose more lives that way, but at least it won't look bad.
He should deliver the news personally. And stay with the grieving family for a few days.
Each Soldier gets an autopenned letter from the President, I believe. Does that out rank a personally signed letter from Rummy? Hum... He is a silly old man way past his due to leave DC.
Signing a few letters every day could be done in a couple of minutes - he could do it at his stand-up desk while having his morning coffee.