New answers tagged us-visa-waiver-program
In theory it is possible! I spent exactly 90 days in the US with a ESTA visa waver (also coming from South America), then I traveled for about 3 weeks in Canada and entered the US with a flight ticket that left 2 weeks later from NYC - there was no problem at all coming back into the country, just make sure you have your tickets ready to show at the border ...
According to Visa Waiver Program Wikipedia page (I assume you can join the Visa Waiver Program) Passport validity The standard requirement for passport validity is 6 months beyond the expected date of departure from the United States. However, the US has signed agreements with a number of countries to waive this requirement. 
Yes, no problem. You can exit and re-enter during the 90 day limit, and in fact if you leave North America (USA, Canada, Mexico) the 90 day period resets. You just need to make sure your ESTA is valid for the entire period as well (they're usually valid for 2 years) and you have evidence of your travel plans and finances are in order.
It is legal to look for work whilst in the US under the Visa Waiver Program, however it is NOT legal to actually work whilst on the WVP. If he is offered any form of employment within the US he will need to return to his home country and apply for a work visa for the US. Depending on the specific situation, obtaining such a visa will be somewhere between ...
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