In planning for this trip several resources come to mind. Bootsnall.com is an around the world (ATW) planning site that sells package tickets and offers advice on long term travel. We elected not to buy the ticket but took their class on things like how to get a next country visa while traveling, ATW insurance, packing, travel safety, having proof of onward travel, money, budgeting, travel burnout, using hostels, etc. All of our clothing had to be pretested for weight, quick drying, and durability. Of course things that dry overnight in Colorado take 3x more time in the tropics so we had to bring a 3 day supply of clothing to ensure we had something clean to wear. Anything made of cotton or leather will mildew in 3 days so only nylon and poly fabrics allowed.
Bootsnall.com talks a lot about travel burnout and how to pace sightseeing with relaxation days. They recommend a budget of 3x your daily hotel cost, so pretty cheap in Asia but outrageous in Hawaii. Most countries require proof of onward travel and there is a website that will actually rent you an onward ticket for customs use but we chose Kiwi.com for our air tickets. With Kiwi you enter your location and it shows airfare to everywhere else by day. This was invaluable for locations that didn’t have daily air service and places where the cost varied by day of week. We decided to buy tickets two countries ahead and Kiwi emails your boarding passes the night before. We’ve been finding airfare about 10% higher than our original estimate and at least two destinations with a 20 Kg luggage limit. That limit would’ve been fine until we added Milford Sound NZ and it’s 50 degree temps, so now we need winter clothes.
We chose Booking.com for hotels just to make tracking 31 hotels easier with a handful of exceptions that were cash only places. Most of the hotels have full cancellation credit so we can change dates as needed. The one big exception was Patong Beach, Thailand and the notorious “walking” street where the song “One Night in Bangkok” definitely applies. Surprise 100% NON-refundable after we booked. I’m going to assume that is because people cancel and walk away after seeing the hotel. We'll keep you posted on that one.