State of the trip

For anyone considering a similar trip, here are cost-per-country estimates and some other necessary expenses associated with the trip.

Chillin' like a villain in Nicaragua

Insurance

• Health insurance: $1600 for 16 months for two people - Covered only catastrophic events, emergency evacuation, etc.
• Car insurance: $3500 for 16 months - We bought extensive coverage since our car was new; third-party only insurance is much cheaper but doesn't provide much coverage.
  
• Property insurance: $440 for 2 years - Covered any theft of our belongings during our trip.
  

Inca terraces outside of Cusco, Peru

Transportation and shipping

• Shipping the car from Colon, Panama to Cartagena, Colombia: $900 including all shipping and port fees. We shared a 40 foot container with another car; costs may be higher for a single car 20 foot container, but lower for the 'roll-on-roll-off' option.
  
• Sailing from the San Blas Islands, Panama to Cartagena, Colombia: $700 for 6 days, 5 nights on a yacht. 3 days of heaven sailing the San Blas Islands, 2 days of hell crossing the open ocean.
• Shipping the car from Buenos Aires to the US: $800 for a 'roll-on-roll-off'' ferry, including port and paperwork fees.
• Flight from Buenos Aires to Miami: $2000 for two one-way tickets.

Sharing hot chocolate in a family's home in Lagos Montebellos, Mexico

Cost of living

Average budget per day (for two people), including hotel/campsite fees, food, beverages, gasoline, vehicle maintenance, toll roads, and other costs associated with driving.

• Mexico: $75/day
  
• Guatemala: $70/day - If you want to learn to speak Spanish, this is the most economical country. We lived with a wonderful family and took lessons in Xela, but Antigua has a more pleasant climate and atmosphere for those weighing options.
  
• El Salvador: $43/day
• Honduras: $100/day - This value is skewed as we got screwed at the border and spent less than 24 hours in that country.
• Nicaragua: $90/day - One of our splurge countries. We partied with friends over New Years and rented a luxurious condo with our friends Tom and Kelsey to put together our website with driving information, Drive the Americas.
• Costa Rica: $48/day - While this country is probably the most expensive in Central America, we played it super cheap for a month when we squeezed in to a small cabina on Playa Negra with Tom and Kelsey, cooking our own food and catching our catch.
• Panama: $54/day
• Colombia: $64/day
• Ecuador: $78/day
• Peru: $85/day
• Bolivia: $85/day
• Argentina: $95/day - Many long days of driving large distances really added up.
• Chile: $40/day - We were only in one location, Pichilemu, for a week, so this is not representative of the true costs of this country. Chile is more expensive than Argentina.
  
• Uruguay: $66/day - Prices in Uruguay are similar to those in Argentina, but the country is so small the driving expenses were low. We also camped everywhere except when we were playing gauchos on the ranch.
  

Children on the Islas Taquiles, Lake Titicaca, Peru

While this does represent a good chuck of change, we would probably have lost more if we'd left that money in the stock market...money well spent in our opinion.