Now, administrators' efforts to retain teachers have taken on a new urgency as they try to make progress on promised reforms that won Hawaii a $75 million federal "Race to the Top" grant. Teacher retention is one of the keys to those reforms.
They are offering $1,500 bonuses to work in "hard-to-staff" schools and plan to increase that amount to $3,000 next school year. They are also holding classes in Hawaiian culture and language, and teaming new arrivals with veteran teachers to help ease the transition.
"This is a pretty big push for us," said Alex Harris, who is overseeing the state education department's "Race to the Top" efforts involving teachers. "We don't want to be recruiting at a high volume every year and losing professionals in their second or third year."
Hawaii the only state with a single, statewide district has long had to turn to the mainland because local teacher education programs can't produce enough graduates to fill classrooms across the islands, especially in remote schools.
Getting the newcomers to stay is difficult, as they face culture shock, a high cost of living and a vast ocean separating them from their families.
"I recruited hundreds of teachers," said Al Nagasako, who was principal at Nanakuli High and Intermediate School, where Sager taught. "You begin to select the good ones, and you know they're not going to stay."
The U.S. Department of Education criticized Hawaii for not doing a good job of publicizing the bonus for teachers to work in "hard-to-staff" schools, so Harris said the bonus has become a more prominent part of the pitch.
A new recruitment perk targets mainland teachers who can fill badly needed special education vacancies by offering them relocation bonuses, Harris said. The highest amount is $6,000 to work in Waianae or the Big Island's Kau, Keaau and Pahoa areas.
Those areas make up the low-performing, high-poverty schools that "Race to the Top" reforms are focusing on.
After his arrival, Sager, of Warren, Ohio, took a bus tour along with other new teachers and saw the poverty on the Waianae Coast.
Settling in required developing an ear for the pidgin English his students spoke and learning to pronounce vowel-laden names he never heard before. Even as he earned their acceptance, Sager said, he grew frustrated with feeling like he and his students were lab rats for experimental programs.
"We start and it's not perfect, so we scrap it and start over," he said.
State education officials are also offering a mentoring program, which began last school year, meant to help teachers feel supported, Harris said.
Nanakuli teacher Dennis Tynan bonded with a group of other teachers who were also adjusting to Hawaii when he arrived 10 years ago.
Tynan, 46, said the group helped him feel connected to the school. He also attributed his longevity to being older when he arrived from Texas, arming him with more life and classroom experiences. Now that he's one of two left in that group, he's starting to wonder about his future.
But those doubts are eased by his students, who no longer treat him like an outsider. He feels he owes it to his students to stick around.
"Here is a community of a marginalized ethnic group and because of the way everything gets structured in a bureaucratic schools system, they just get screwed over and over again," he said.
For some, the cost of living gets to be too much.
Kristen Wong, who left her job teaching special education on the Big Island to pursue a master's degree at Harvard University, met her fiance in Hawaii, but the costs of visiting their families on the mainland started to seem more daunting as they looked forward to having children.
Wong, 29, worked a second job most of her time in Hawaii to make ends meet. The entry level salary for the current school year starts at $33,169.
"It was really, really hard to make things work," she said. "I have student loans. I have a car loan ... I'm actually pretty fiscally responsible."
Now, state officials are focused on teachers like Owen Allsopp. The 22-year-old graduate of University of Massachusetts at Amherst is settling into teaching first-grade at Pahala Elementary on the Big Island and sharing a house with three new teachers.
Before the first day of school, he already had a good grasp of Hawaiian names and words. And he's aware of the pressure to keep him.
"I know it's so important because it's hard to create lasting change if there's so much transition happening," he said. "There needs to be serious commitment."
Follow Jennifer Sinco Kelleher at http://www.twitter.com/jenhapa .