Earlier quoted context omitted.
The beginning being as soon as they knew their satellite had been deposited well below the desired altitude. If the F9 engine hadn't failed, they wouldn't have needed to do an orbit raising maneuver at all and there would have been no risk of the satellite deorbiting.
A orbit raising maneuver was always necessary to get the satellite to its target. Relevant sections: > "Orbcomm had planned on reaching an altitude of 466 miles above Earth..." > "Due to the engine shutdown, the Falcon 9 used slightly more fuel and oxygen to reach Dragon's intended 202 mile- (325-km) high orbit. Over the next 2.5 days, Dragon flew itself to the station's orbit 250 miles above Earth. It reached the $1…
The expected outcome (F9 upper stage doing the raising) was considered non-risky, and I'm sure that's the premise the insurance company was operating under when they agreed to insure the satellite.