I heat seal my cookies. I haven't considered vacuum sealing/shrink wrap because of piped details on the cookies would be damaged under the pressure. I developed a recipe which produces a softer cookie which keeps fresh for an extended period of time, while still holding up to supporting the icing and stacking. I use backer board inside the bag on delicate shapes (palm trees, horseshoes). I only heat seal my cookies, no exception. I do not twist with a ribbon since the bag is not sealed, which means air can get in and dry the cookie out. I am in a desert, so my climate is very dry and I am cautious about my cookies drying and hardening.
I operate my business as a Cottage Food Operation, and I have a full time job. I have determined my maximum cookie count is about 100 in a week. I also take a week off between orders. This way I do not take on more than I can handle, plus I have a recuperation period between orders.
Before I went into business I experimented with freezing and determined what I feel comfortable freezing. Non-decorated, flooded, finished, light colors, dark colors, bagged, not not bagged - there are several variables. My dry desert climate impacts my results. For personal use, I freeze completed cookies, stacked, not bagged in storage containers. I ate a thawed cookie that was in the freezer for 2 months, it tasted as fresh as the day I put it in the freezer.
I don't ship, it's against the Cottage Food laws in California, but I still reserve a few cookies and will eat one the day of the event. Also if the client/their guests eat one and two days after - I like to know what condition the cookie is in.