You bring up some points I had not considered! We are driving, so weight is not a great concern, and, since I am only focusing on myself, I am thinking it may be too soon to think about a packing dry run. I will be travelling with two growing boys and every time I try to think about which of their current clothes will come with us, I just end up shrugging and wondering how much taller they will be in the fall! I do envision a miserable, "do we have to," last minute shopping trip for the boys in the fall. (Maybe I should get that date on my calendar now???) But, I am still wrapping my head around having to pack bulkier clothes, so a packing dry run is not a bad idea. I have over packed for every cruise we have been on, and, because of the fall items, I really want to minimize what we take.
I hadn't thought about mix and match -- my focus is really on dinner outfits and what to wear for the drive, so I was planning to photo the whole outfit, with my phone, but ultimately to drop the photos in my spreadsheet. I haven't had a chance to start yet, but I will let you know if this ultimately ends up being a waste of time!