So he complained about working in a Deli,

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He kind of got what he always wanted, he wanted his own restaurant, this is kind of it. And if they have good food, those food trucks can rake in serious money. People are obsessed with those things and will line the block to pay for some expensive little plate of food.

Why didn't he try to find another job at a fine restaurant while working at the deli? There are dozens of fine restaurants in Ann Arbor alone then there's Detroit which is only a 45 minute drive. I realize this is how it was written but he essentially gave up his career and self respect within those first days after he stopped looking for work as a chef after he was hired at Zingermans. He spent years in school, putting in countless hours working his way up the ladder to be a head chef in San Francisco, then threw it away upon arriving in Michigan. I can't imagine anyone giving up so quickly after all that. The relationship was doomed from that point on.

Food trucks don't all sell crappy burgers. Working in a crap deli doing boring sandwiches for a guy who was schooled at the CIA is like asking an air force pilot to drive a school bus.
He was doing interesting food in his own food truck. Doesn't have to be a snooty restaurant to be fun.