Ecuador: Your guide to the "new Costa Rica" {Gadling}

Aug 9th 2011 1:36PM Aaron,
The wife and I would like to check Ecuador out, leaving from Tennessee, USA. Any Idea about the cheapest way to travel to Quito? We would be hoping eventually to live in the Cuenca environs and want to check out the possibility of living, not necessarily with expats, but with the locals and adopting a lifestyle that would allow us to blend in. We've thought of driving our Prius down the Pan American Highway, and then renting (maybe buying after we make a final decision) a furnished place while we check the area out and then getting into an unfurnished unit (house, apt. condo, etc) and furnishing it locally. Do you think that's too dangerous, especially the Mexico portion of the trip? Our income, unless one of us works is around $36-$37,000.00/ annually. Do you think it's reasonably do-able?
I know this is a long query, but thanks for any portion you care to address,
Dean