Gathering stuff

Personal items: How exactly do I take enough vitamin D (and other routine meds) for a six week trip?

Conference items :  How many brochures are necessary and how many equal sacrificing one outfit?  I got a new conference tablecloth - it's a "runner" this time. Much smaller to pack.

Clothes - and the big one - shoes.  Can I managed to pack all outfits that go with black shoes?  or do I need black and brown ... and blue?  do I need flats besides sneakers? flip-flops?  The plan now is to begin laying out outfits complete with the socks, shoes, jewelry and make-up that will go with them.  I used to laugh at my mother for organizing her outfits this way in the closet.  But now I'll be doing it in my office.  Then pack everything into the suitcase and weigh it.  Then take it all out and add or remove outfits. Repeat.  Doing it now in case it turns out there is some critical component that I will have to buy.

Do you suppose it is really possible to organize this trip completely in advance?
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