Crispy fried chicken goes limp: picnic disaster

Once fried chicken or any fried food for that matter is refrigerated it is going to lose it's crispiness. This is due to the cruncy exterior coating absorbing moisture from inside the food combined with moisture being trapped inside the wrapping/storange container which then is absorbed by the food as well. It happens even shortly after frying if the food item is placed on a flat surface where the inner steam can't escape and is trapped between the food and the surface under it. This is why when frying large batches or holding fried food for any extended time, it's best to drain on a cooling rack that's upside down on a brown paper bag or paper towels. Upside down so that it's close to the paper to absorb excess grease but still allows a small bit of airspace so that steam can escape and if keeping it in a warm oven, hot air can circulate.

You can re-crisp your chicken by placing it on a roasting/cooling rack on a baking tray and place in the oven to re-crisp the skin. Be careful not to dry it out.

The first part of the solution is not to cook it as close to eating time as possible.

After that, you're fighting to dry the skin as fast as it gets moist.

Dry as thoroughly as possible after cooking.
Wrap in cotton napkins that will help wick away moisture.
Keep in a loose weave basket. Obviously, this is not compatible with keeping the chicken in a cooler, so again, the shorter the time-frame, the better.

It sounds like your double-dip method is a double-edge sword. It makes the chicken phenomenally crusty, but that crust is then a giant sponge for water. Darin's quick-roast revival sounds like the solution.

Okay I'm answering this super late, but crisp fried chicken is not bound by time :) So what works for me is

1. Fry it with a starch; something like a potato starch or corn starch or even rice flour rather than regular flour.
2. Fry it fresh. Have as little time possible between frying and consumption.
3. Dry it out on a rack after double frying it. Proper air circulation provides great crispness.
4. Once it is at room temperature, pack it immediately in airtight ziploc bags by vacuuming it either by plunging it into a bin of water or using a straw to suck out air. You could also add food grade dehumidifiers (even silica gel is safe to use)

Although your chicken will eventually get limp cause the crust will absorb moisture from within the meat; these steps will ensure it doesn't absorb moisture from the air. Another thing to do is to double coat it and create a barrier between the meat and the crust (similar to having a layer of chocolate on a tart crust) by having a primer coat of egg white + corn starch batter that is fried till crisp and hard and then proceeding to give it another proper flavorful crust.