Teaching A Man to CVS

I posted not too long ago about our goal of budgeting $1200 for the year for all grocery, HBA, paper goods, etc. I also told y'all how Dan had agreed to do a major part of the heavy coupon shopping. Now he is awesome at Kroger; as long as I send a detailed list and have all the coupons together, he does great. But today we were discussing CVS. Now CVS shopping is going to play a big part in keeping us on this budget. I mean, CVS should keep me from having to pay for HBA and will probably end up making me money. Poor Dan does not understand how to shop at CVS. He's seen me do, he loves to come along and watch me, but he's not so hip on doing it by himself. I tried making him a detailed plan, but there is to big of a chance they will be out of something on the list and he doesn't know how to rework the plan. So, what should I do? Do I keep trying to come up with several different scenarios, hope one works and he can do it on his own? Or do I make a 60 mile round trip to do it my self? There are some good deals this week and I have expiring ECB. I think the CVS factor in my budget is going to be harder to manage than I'd thought. Any suggestions?