To keep your moist cookies soft and chewy, place a quarter slice of bread (per dozen) into the container. The cookies will absorb moisture from the bread, keeping them soft longer. White bread is best, as it won't transfer its own flavors to the cookies. You can replace the bread when it starts to harden (if the cookies last that long!).
When you're packaging your cookies, don't just pile as many as you can into a tin. You'll quickly find yourself eating peanut butter-flavored shortbread cookies… which is only good if you made peanut butter shortbread cookies.
If you need to get all the cookies in one tin, pack each flavor into individual freezer bags. Freezer bags are thicker and less porous than storage bags, which will ensure your cookies taste exactly the way you intended. Just try to get as much air out of the bag as possible.
Pre-packaged food companies have the same concerns you're having now. They've spent a lot of money on research and development, so leverage their expertise to your advantage. Cylindrical chip containers are about the right diameter for most cookies and come in tall and snack sizes.
When you're finished with your chips, wash the container. You can stack several cookies in each canister (depending on the size). If you're giving them as gifts, you can use pre-cut contact or wrapping paper to cover the outside. If you're shipping them, place a small square of bubble wrap or bread on the bottom, between each cookie, and on top. If you opt for bubble wrap, you may wish to wrap the cookies individually in plastic wrap first.
When you're storing cookies, try to keep the type of cookie in mind. Not only should they be separated to avoid flavor-mingling, different cookies have different needs. Bar cookies should be stored in the container they were baked in. So if you're giving them as gifts, use appropriately sized disposable metal containers. Soft cookies should be stored in airtight containers, while crunchy or hard cookies should be stored in easy-to-open containers (like a cookie jar). Also, if you have to stack cookies in the container, they should always be separated with wax paper to keep them from sticking together.
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