I'm in the process of planning a huge trip in the summer of 2011. My boyfriend and I are from the UK and have purchased ONE WAY tickets to New York (via Iceland) and plan to travel from New York on to Toronto, across Canada to Vancouver then down through the states to Mexico and continuing south through Central and South america. We will be purchasing return tickets just before we travel as we'll have more of an idea of what budget we have and how far we can go.
Unless you have tickets showing that you are traveling out of the country, it is likely that you will be requested to purchase such tickets upon arrival in New York (and probably from New York directly back to the UK).
To avoid this, I'd do what some others on this site have done and purchase air tickets from south Florida (Miami or Fort Lauderdale) to the Bahamas (either Freeport or Nassau)--a very cheap route--to show that you have complied with the terms of your VWP. Whether you ever use these tickets or not--they will at least show that you plan to leave the country.
P.S. Someone on here said that they were able to get such tickets via a low cost charter company for about $50 each. This will be worth it, allowing you to comply with the rules while still keep your options open for actually leaving via Mexico and then going on to South America.
P.S. Be sure that your tickets to/from Canada are also both purchased at the same time--whether you go by bus or by air--otherwise this may also cause you a problem.
Good luck and enjoy your trip
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