One other thing you might want to look into as you plan for this trip - the various visa requirements for all the countries you are planning on passing through. Generally you only need a visa if you will be staying more than 90 days in a country, but that isn't always the case.

Plus, if you will be passing through a country like Mexico both going and coming back, make sure you don't run afoul of any regulations on back-to-back stays that add up to 90 days. Also, if your plan to continue to work (even online) may run afoul of any local laws or subject you to taxation. Chances are that you'll be able to exempt your earnings during this time on your US tax returns, but you may want to talk to a tax advisor before you go to make sure you are straight on the requirements.
Cheers,
Bev