I'll be "in between jobs" soon and I'm considering doing something similar. This thread literally brought me one step closer to leaving everything behind...
I've got a few (quite practical) question, if you don't mind:
1) I've seen this graphic of your total/avg spending on your blog. That caught my attention because the spending is so incredibly low - how did you manage that? I've got three big topics... first: accommodation. I guess couchsurfing (i.e., staying somewhere for free) is a big part of it, but what about the 12 bucks a day in the US? When I was there I felt that even AirBnB is not very popular, and cheap hostels are hard to find (as opposed to, for example, Brazil or many other countries). And if you find them they're easily 20-40 bucks depending on the region. Incidentally, 18 avg in Brazil is relatively high, so I guess there you went with hostels/backpackers, but it was the highest overall on your trip! So... what's your secret for other places? I know that in other South American countries couchsurfing works well, but what about Canada?
Second, food also caught my eye. Did you consciously make an effort to minimize food spending, or is it just the result of always getting the first best choice - street food, simple restaurants? It's not difficult at all to get by with 9 bucks per day if you just eat arroz com feijão every day, but one trip to a churrascaria (which is a must if you stay in Brazil in my opinion) is 20-30 already. Or did you get some free meals due to couchsurfing?
Third, what's not included is travel - the flights in between locations, but also the bus/train tickets within a certain country. Can you estimate how much one needs to keep in mind for that and if there are any tips and tricks to consider? Blue ticket was something I always had in mind, but just realized it's not an option anymore due to the age thing ;-)
2) Many people prepare such trips way ahead of time. Can you - off the top of your head - name a few things one absolutely *has* to prepare well in advance? Like - what has to be done 3 months before, 6 months before and so on.
Seriously, your blog is such an inspiration (and has been for many years before, just naming Kilimanjaro here ;-)). Absolutely amazing stuff!