I told Heather to lay out everything she wanted to take, then put back 1/3. It was still too much. No need for different clothes every day except for dinner. Day clothes = tevas, swimsuit and shirt almost everyday.
Go out at least a day early. Why spend the first day of vacation on a plane all day? Time of year was great (we have also done Sept which was equally nice). There will be some differing opinions, but I don't believe the balcony is necessary since everyone is out on deck or on the islands anyway and this isn't a sailing cruise. Don't try to squeeze everything in every day. It will ruin you for the night fun.