Originally Posted by
FatnLoud
In terms of "resetting", there are restrictions on what constitutes leaving the US. Simply going to Canada or Mexico is not allowed and I believe neither are some Caribbean countries, not sure about Costa Rica.
The US Customs & BP explanation of the visa waiver program that I read explicitly says that Costa Rica counts as a reset if it doesn't look like you're only there to get around the 90 days rule. Impression I get is that it's not an outright recommendation but along the lines of 'if you're going to try to do this anyways, at least it's a relatively safe and fairly developed country with good air links to the USA'.