How to pack for a 3 month trip abroad...we think

We've had quite a few people ask us how we're going to pack for our nearly three month long trip to Hawaii, Australia, and Thailand. With packing there's always a fine line between want and need. And, of course, it's important to reduce weight as much as possible for both travel comfort and airline restrictions. After much debate we've settled on the following, and we hope we're happy with the result: 

Our climbing gear: quickdraws, route cleaning gear, chalk bag, belay device, climbing shoes (and Brandon's chucks), harnesses

We struggled to choose a bag for our climbing gear until Brandon had the ingenious idea of using our rope bag and attaching our climbing helmet to the outside. We're not bringing our rope, because it's heavy and we can buy one in Thailand. The bag is small enough that we're hoping the airline will consider it to be a free "personal item". 

Brandon's items. Row 1: bathroom bag, tooth brush, medications, travel first aid kit
Row 2: 9 socks (3 thick Smartwool, 3 sport Smartwool, 3 light & thin ), 10 boxers, 1 sweatshirt, 2 long sleeve shirts, more toiletries
Row 3: hand towel, washcloth, 2 athletic shorts, 7 shirts (1 Icebreaker wool) , hat, sunglasses, wallet
Row 4: day pack bag, 2 shorts, swimsuit, climbing pants, jeans, Keen sandals, laptop + cord

All of Brandon's items fit in this backpack!

Katie's items. Row 1: running shoes, Chacos.
Row 2: 2 bras, 3 sports bras, swimsuit, 10 pairs underwear, 4 pairs socks, dirty laundry bag, ubiquitous blind date scarf.
Row 3: 6 t-shirts, 3 sleeveless shirts, 2 climbing pants, 2 running shorts, 2 workout shirts, 1 Icebreaker wool dress, 1 undress
Row 4: lock, diva cup, toiletries, spare glasses, 2 life straws
Row 5: 2 pairs of shorts, 1 pair jeans, 1 pullover, 1 sweatshirt, 1 raincoat, 1 multi-use headband
Left side: large empty duffel/backpack for re-distributing items as needed for weight-based flights

All of Katie's items including the empty bag fit in here! 

Day pack: water bottle, plug adapters, headlamps, wallet, passports, international drivers license, phone, power cords, toilet paper, rain poncho

Everything we think we need for about three months of travel!