I am just catching up on posts today, missed Sunday posts altogether working on a project. So didn't scroll down to see who else posted answers and hope I'm not just duplicate posting. LOL
1 - I bake off and on through out the month. I ship some of baked goods, so those I do earlier in the month to make sure they arrive in time.
2 - Freezing depends on how early I make them. If it's just a week before Christmas, no I don't freeze them. They usually don't last that long. LOL
3 - Depends on the type of cookie. Some cookies like highly decorated sugar cookies I would never put in a freezer bag because they would break. I use storage containers. Others, I do use freezer bags.
4 - The cookies I store in the kitchen or fridge I use storage containers.
5 - The cookies I leave out on tables, I use cake plates with domed covers. Makes the display very pretty and it's hard for people to not put that back correctly. I also like cookie tins, they're pretty, traditional, and work great for keeping cookies fresh.
I don't think I've ever had sugar cookies go stale or get hard. Are you referring to the ones that you put out and are covered with plastic wrap? I could see those eventually going stale, but I've never had that happen with storage containers or the cookie tins.
In regards to the chocolate chip cookies - I freeze the batter. Mix the batter, pop the whole bowl in the freezer for about 7-10 minutes while the oven in pre-heating. Not rock hard, frozen, just stiff. Scoop them out for the cookie sheet, bake, I let them cool on the sheet for about 5 minutes. Then transfer to a cooling rack. In the case of chocolate chip cookies I always store them in an airtight container or storage bag, with a damp and rung out paper towel. The cookies absorb the moisture from the towel (if they last a few days you'll find that the towel does dry out completely over a 24 hour period), and they stay very moist instead of getting brittle and crisp. I like choc chip cookies to have a bit of crisp to the edge, but for the most part be soft. My chocolate chip cookies stay about 1/2"+ thick. Several times I did freeze them too long and had a batch on a sheet that stayed smaller because they wouldn't spread. LOL