Thank you for your responses.
econlady, may I ask why double bag them? I use a gallon freezer bag. Should I double that?
I freeze the finished ones, but had never frozen undecorated ones. With choosing to do 2500 this time, I had to look into different options. I baked 1500 and froze 500, vacuum sealed A LOT... big mistake!!! They stuck together and we lost a lot of them to breakage trying to pry them apart. If freezing them 2-3 times prior to shipping, that would be ideal.
The hand drawn ones I'm afraid would run/smudge since it's just food color/edible markers. I'm clueless how to protect the writing from possible exposure.
Double bagging is to protect from freezer taste. When freezing I layer the cookies, with parchment paper or wax paper between the layers. I take them out and defrost them on a rack. When fully defrosted, and at room tempature I individually bag them (heat sealing the bag) and prep for delivery. When packing to transport , typically I layer the cookies sideways. I do put bubble wrap between the cookies. Going sideways and using bubble wrap I have less breakage. I've taken 130 cookies across the country and had no breakage. I believe it is because I can pack the cookies tighter.