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A retired army general who knows me quite well is writing one of my recommendation letters - if he is willing to write school-specific letters to my top 4 or 5 choices, should I ask him to do so? Obviously he would just tweak the original letter to include school-specific material and references, but I'm not sure how much impact this will have.

Thanks!

I don't think it's worth making him to go to that much trouble. Unles HE actually knows something specific about the school (like he's an alum), he's just going to be regurgitating something you give him. Better to let him write about YOU in his words.

It will have zero impact. Worth doing if the recommender is an alum, otherwise don't put the recommender through the trouble.