A few things I would make sure of:

1. Vaccinations - make sure you have had all the shots you need, and obtain any prescriptions you might need (including maybe some 'just in case' meds if you are going to be off the beaten track). Some of your destinations will need anti malarials, not sure how long those tablets are good for (i.e. if you can get them before you leave). You may also need Yellow Fever certificates travelling between some destinations. Some vaccinations need time between them to give you full cover, so you might want to look into getting them done sooner than later. Make sure you tell the travel doc that you will be staying in budget accommodation, and may be off the beaten track - things like rabies shots may become more relevant than for your average 2 week holidaymaker.

2. I am assuming you live in Vancouver - your BC healthcare will expire if you are out of the country for that long (you have to be physically present in BC for X months during the year. A lot of Canadian health insurance policies are contingent on you having valid provincial health care, and I know people caught out by this when their home health cover expires due to being out of country. I really do think you need a good health insurance plan - a lot of the countries listed present possibilities for weird and wonderful diseases, but completely aside from that you can get hit by a car in any city in the world! Having good medical coverage is an essential investment IMO.

3. Make arrangements with someone at home to be able to do things on your behalf (e.g. at your bank) just in case you need to. Have a spare credit card kept completely separate from the rest of your belongings as far as possible (e.g. one on your body, one in your bag) - I even know someone who sewed an emergency card and cash into their clothing (that seems extreme!). Keep a copy of your passport in the same place. I also make sure I have a copy electronically in a drop box.Whilst kinda archaic, travellers cheques are still accepted in lots of places, and are insured if you lose them / they get stolen, so might not be a bad back up plan.

4. Visas - plan out what you need to get and when, and how. Some countries you can apply for electronic visas (e.g. Australia) so you don't need to part with your passport, but other countries still need you to send your passport in. In some countries, you cannot be a visitor and not have your passport (i.e. you have to have it with you at all times) and I would *never* want to be in a country without a passport in case I had to get home in an emergency (e.g. ill family member) or if something bad happened where I was (terrorism, war breaks out etc.) Some visas can only be obtained within x weeks of travelling (and may require proof of travel), other visas can be obtained ahead of time and remain valid for months. All to say, the visas are probably the biggest thing that will impact the order, duration and timing of your trip.

5. Don't forget you still have to do some real life things (like filing your tax return) no matter where you are in the world!