Financing…i don’t know just put it on credit cards or take out a loan and send payments home monthly and have a family member pay it as the note comes due each month. As far as a job I don’t know exactly what part of Latin America you are going to but while I was on vacation in Mexico I was offered a job at a Howard Johnson Hotel on the beach making $60.00 a day which is awesome pay because most people make $50.00- $100.00 a week even with a degree in mexico. Hope this helps. I didn’t take the job I love my home too much here, but it was interesting.

Wherever you go, look up “(English) Language Schools” in the phonebook.
You may not be allowed to work without a permit, but schools - always in need of native speakers - may/can/will find a way around it.

I suggest you to finance most of your trip from your savings in US $. You can work as English teacher in any Latin America country, but you are not going to get enough money to travel a lot.

Why not be an ESL teacher? You can travel to lots of places and work as you go!