The loop-hole going to Canada and return to get a new 90 day stay has been closed. Visits to Canada, Mexico, Bermuda or the islands of the Caribbean do not prolong the authorized stay.The status of a visitor on a 90 days stay under the Visa Waiver Program cannot be changed or extended in any way; he would need to go back home or to a country outside of the Western Hemisphere.http://www.cbp.gov/xp/cgov/travel/id_vis�� ..However he could travel to the United States on a B-2 visitors visa and declare on entrance that he is planning to change his status should the contract get signed.http://www.uscis.gov/portal/site/uscis/m�� ..
I have been speaking with a friend who is Irish and has been thinking of coming to visit the US. She has mentioned visiting Canada for a few days then re-entering the US.with a fresh 90 day visa. I am not sure about the requirements but I know going to Canada is a lot easier than flying back to Ireland and returning. Plus the record label if he is signed would have a legal department and probally would do their best to change his Visa from a visitor to a Artist visa.