So sorry about your situation! One thing I wanted to add, is based on what I have been told, if you do freeze them you should let them defrost completely in the freezer bag before taking them out. You will likely have humidity there in HI and need to be careful. If you wanted to freeze them after decorating, I would make sure that they were completely set before freezing, heat seal them in cello bags (not plastic) that you are going to use and then place them in freezer bags. Again, I have not done this officially. This is one test I did just to see how it worked. The taste was 'okay', but not as good as fresh, which is what I needed. However... I was not trying to do 200 and living at my in-laws.
Can you do a test run with a few cookies, freeze them as mentioned above and see what you think? I like the idea of trying to do a test run also as you mentioned that you are newish to cookie-ing and 200 is a large number. Any time I plan to do a large number, I find that doing prototypes so that I can work out the steps ahead of time really helps. I think your design ideas sound so very cute, but just be careful not to overextend yourself. You might be biting off a pretty big chunk here and that would be my only concern as I did that back when I was starting out. If you find that 200 with a variety of designs is too much, might I suggest focusing on one simple design? Again, what you are doing sounds so cute, but you might want to keep that idea as a back-up. Just a thought. So I would try freezing in cello, sealed in freezer bags, bring to room temp in the bags. Take them out, tie on your ribbon or tag and you would be good to go. Again, I haven't done this 'officially', but if you are going to freeze after decorating, this might be a good option. Again, just my thoughts.
A test run is the best way to go if time permits and when you do your planning calendar, allow extra time. That always helps me. If I ever do freeze, I will freeze the unbaked cookies, bake them and then decorate. It only mentioned the 'freezing after' idea as I see it mentioned. I just thought the cello bag and defrosting completely in the bag first would help.
"I think every woman should have a blowtorch." - Julia Child
"I think every woman should have a blowtorch." - Julia Child