I have been through this many times. One thing you really need to watch out for these days is the dimensions of your suitcase and the weight. Airlines are enforcing the limits more than they used to, and the weights have gone down. It is easier than you think to put more than 50 pounds into a suitcase. Dried fruits, nuts, and candy are heavy. So be sure to measure and weigh--if the airline decides to be picky the excess charges are enormous. But you'll probably be okay. (Where I always have trouble is coming back!) Use a relatively lightweight suitcase as you don't want to waste your precious weight allowance on a heavy one.I always bring a big suitcase (although if you don't watch it, a 28-incher can exceed the total dimension limit if it is an expandable one and you stuff it to the gills). The main problem with that is that you then have to figure out what to do with the suitcase until you come back from Japan. I use a combination of takuhaibin and leaving it with family. I never travel around in Japan with the big suitcase. (I use a backpack plus sometimes a folding duffle bag.)
Another thing I recommend is to use a large corrugated cardboard box (or multiple cardboard boxes) inside the suitcase. This keeps the omiyage nice-looking during transit (a smashed box of chocolate or a package of whole nuts that has been rendered into fragments is not a nice gift). The same box is invaluable for lugging things back. I bring back all kinds of rice crackers and other fragile food items, and they hardly ever break. This is simply not possible if you use conventional cloth or vinyl packing cubes or plastic bags to compartmentalize the stuff. Airlines are ruthless. The cardboard box trick may seem fussy or excessive, but I have done it many times and it is one of the best packing discoveries I have ever made. I use one big box that is as large as the suitcase will hold, and then nest others inside it. Outside of the big box I usually put some of my clothes and other items I use while traveling. When I collect my suitcase at Narita I sometimes take a few items I need out and then send the suitcase to the family via takuhaibin. (Not sure if this will work in your case. Be sure to warn them in advance at any rate.)
Omiyage for five families is a lot! You are wise to start thinking about this in advance and have a plan. I always spend a ridiculous amount of time preplanning luggage logistics, but as a result my trips go smoothly.
I have never had to show food (or anything) at customs in Japan, by the way. But I suppose it is good to be prepared for that. The cardboard box trick will make it easy. (And like AK says, watch out for beef jerky. It is a red-flag item.)