I'm currently in the US on a F1 visa, doing OPT. My work permit expires on July 23rd and I decided to go back to my home country. The "problem" now is that I've already planned a vacation with my family in Florida at the end of November, but my 60 day grace period for my F1 status ends on September 21st. It makes more sense for me to stay in the country until the end of our vacation rather than going home to Germany and having to deal with the unemployment department.
Of course I don't want to stay in the county illegally and I applied to some school with ESL programs since it's probably the easiest way if I continue school and maintain a legal F1 status. Now I worry that I won't get accepted at a school and my Plan B would be to visit a friend in Canada for three weeks and enter the country in mid October on the VWP. Is there some rule about how long I have to be out of the country before I can enter the country again on the VWP? How high are my chances that the officer at the airport let's me enter on the VWP three weeks after I left the country with an F1 status?
Thank you for your help.