formerlyknownas
How will it look if I asked them for one more recommendation. This new recommendation has similar questions to the rest. I want to ask them to cut and paste their responses to the other recommendations but I am afraid I'll give them permission to do a shoddy job. What do you think? Is asking one person to do four recommendations stretching it?
I really don't see how this could be a problem, unless you are on uncertain terms with your recommender. If he's done three, he will probably do a fourth.... at least that has been my experience.
Round 2 deadlines are almost 2 months away - why not just make it easy for him? Tell him in person, then send him a thorough email stating the questions he can expect and what you think would be good points to address in those questions. Wrap it up with a bottle of single-malt scotch (Macallan 18 year old is a crowd favorite and surprisingly neutral). If there is one thing I have found in life, it is that people will be your friend in return for exotic alcohol.