Updated

Transportation records show the flight instructor for a New Hampshire pilot charged with killing his daughter in a Massachusetts plane crash repeatedly denied his requests to fly solo.

The instructor told federal investigators 57-year-old Steven Fay of Hillsborough should not have been flying his twin-engine Cessna without an instructor on board and that that he was "crazy" to be flying the plane at night.

Massachusetts prosecutors are charging Faye with involuntary manslaughter in the crash at Orange Municipal Airport that killed 35-year-old Jessica Fay on New Year's Day 2011. The crash occurred 90 minutes after sunset, after the plane clipped treetops on descent.

Fay told The Associated Press he loved his daughter and has been grief-stricken since her death. He is scheduled to be arraigned Wednesday in Greenfield, Mass. Involuntary manslaughter is a felony punishable by up to 20 years in prison.

Fay did have a license to pilot single-engine planes, but the Federal Aviation Administration issued an emergency order revoking that license two months after the crash. He had obtained the license in 1989.

That emergency order, dated March 22, stated Fay lacks the "care, judgment, responsibility and compliant attitude" required of a licensed pilot. The order notes that he was not authorized to fly solo, carry passengers and was not current on flying at night. It notes his last night flight took place in the year 2000. The order also criticizes Fay for failing to familiarize himself with the airport.

"You have a blatant disregard for the regulations airmen operate under and present an immediate threat to aviation safety," the order states.

Fay's daughter was pronounced dead at the scene. Fay suffered bruises to his lower torso and legs, according to National Transportation Safety Board reports on the crash.

The NTSB reports indicate Jessica Fay did not have her seatbelt fastened at the time of the crash. Steven Fay told them she had been trying to locate his navigational chart in the back of the airplane as they approached the municipal airport.

Massachusetts State Police say her body was found outside the plane lying in a brook, her legs pinned by a fallen tree.

Truman -- who would fly from Norwood, Mass. to instruct Fay on piloting the Cessna -- told federal investigators had asked him "numerous times" for permission to fly solo but Truman refused. Truman told them he felt Fay's "old airplane was still too much for him and that the Cessna 310 was a difficult plane."

Fay would not comment Tuesday on Truman's statements that he repeatedly refused to give Fay permission to solo.

"I can't really comment on what's accurate or not until I at least have a chance to go to court about it," Fay told the Associated Press. "I've been sick for over a year now over losing my daughter and everything else, because I loved her very much."

Rick Bendel, a flight instructor who owns Monadnock Aviation at the Keene airport where Fay kept his plane, told the Associated Press he refused to work on the plane in the fall of 2010 because it required so much repair.

"The aircraft would not be worth the money spent on it. It seemed to be in such poor condition," Bendel said.

"We could see the nightmare coming," Bendel said, of Fay's intent to fly the plane.