Something similar happened to me recently. I voluntarily left my job at a US employer, planning to move back home (to Sweden). But first I wanted to spend some time preparing for the move and waiting for my wife to wrap things up. The rules say you have to leave the country the last day of work, so I left for Canada to stay with a friend, and planned to come back on the visa waiver program. I consulted with the compa…
I've tried to do this many, many times, and the rules specifically say you can't just cross a land border to Canada (or Mexico), then come back again.
If you could, everyone would get their 90 day visa waiver, and just hop the border for a few hours then come back and get 90 days fresh.
Last time, I flew to the Bahamas for a week, then came back, no problem.