Now, nearly two years after the attack, Wolf said he has decided to file a claim with the federal victims compensation fund - an extraordinarily difficult decision still facing hundreds of other families with a deadline less than four months away.
"It requires me to bring up a lot of stuff, but it is also closing a chapter on my life," said Wolf, whose wife, Katherine, worked at the insurance and investment firm Marsh & McLennan. "All these files I have kept will be able to leave my apartment."
Dec. 22 is the last day families may apply to the fund, created by Congress to provide financial aid to the families of those killed or injured in the attacks, and to protect the commercial aviation industry from crippling litigation.
As of late August, 2,275 claims had been filed. But roughly 1,700 families had yet to decide whether to enroll with the fund or join lawsuits against the airlines, security companies and government agencies.
The average payout so far has been about $1.5 million, with the highest award $6.8 million. The minimum payout is $250,000.
The lawyer administering the fund, Kenneth Feinberg, has scheduled a cross-country campaign this fall to persuade the undecided to apply.
"I will urge them not to wait, not to procrastinate," Feinberg said in an interview with The Associated Press. He said he hopes to enlist 90 percent of those eligible to sign up.
Monica Gabrielle of Connecticut, who lost her husband, Rich, insists she will not be one of them.
"How do you close a book on the horrific circumstances of 9-11?" she asked. "You have no idea how deep my anger is, not just about what happened, but by how it was handled afterward."
She and about 80 others to date are determined to use lawsuits, not simply for compensation but to pry answers from the airlines, the government, and the agency that operated the twin towers.
Between Wolf's grim acceptance and Gabrielle's search for answers are the hundreds still considering the delicate legal, financial and emotional equation.
"They are suffering, and they are putting it off," said lawyer Justin Green, whose firm represents roughly 500 families. With his firm now filing about one claim a day with the federal fund, Green said he expects a wave of new filings around the Sept. 11 anniversary, and then another just before the December deadline.
"Their choice is to either take that money, or risk everything in litigation where they might not get anything," Green said. "It's a rare family that is saying they will give up $1 million to try to get $5 million."
A small minority of families have decided to do nothing at all - forsaking both the guaranteed payment from the fund, and the hoped-for vindication from a lawsuit.
Margaret Britton, whose sister-in-law Marion Britton died aboard Flight 93, said her family doesn't blame the airlines, and doesn't want taxpayer money.
"Some people think it's strange, but we just felt that in this case, it wasn't anyone's fault, it didn't warrant a lawsuit," Britton said. "We were not financially tied to my sister; it wasn't like she was the breadwinner for the family."
In the initial months after its creation, the fund was the focus of criticism from family members who said its cold calculus to determine cash values for the dead and injured was inadequate.
Some complained everyone should receive the same amount, whether they were low-wage restaurant workers or seven-figure stockbrokers. Others argued the fund cheats families of high-earners out of their true value.
But much of the criticism has dissipated with time. Wolf, for one, said he has seen greater compassion from Feinberg, and improvements in the interpretation of the fund's guidelines.
"I will be working to convince as many people as I can to apply for the fund," Wolf said. "I think some people are really going to regret it if they don't."
Feinberg said he fears many will miss the Dec. 22 deadline, and be locked out of the fund forever. As part of his recruitment effort, Feinberg will maintain extended hours for fund offices in New York, New Jersey, Connecticut, Massachusetts, Virginia and California.
Lawyers for the families believe he will have a hard time persuading the majority of one particular group - those who died aboard the planes - to enter the fund.
Most experts believe the survivors of those who died on the planes have a better chance in court because the airlines had a stronger legal obligation to protect them than the people who died on the ground.
The legal language creating the fund also inadvertently encourages the victims aboard United Flight 93, which crashed in Shanksville, Pa., to sue.
Under the most common interpretation of the fund law, each plane is covered for $1.5 billion in liability by the government. Since Flight 93 carried only 40 people, and caused no loss of life on the ground, each family from that disaster could receive a significantly larger portion in court.
Alice Hoglan, who lost her son Mark Bingham on Flight 93, has decided to sue, even as her ex-husband, Mark's father, has filed with the fund.
"People say the fund is quick and easy and safe - well, I don't want that," Hoglan said. "I want the truth... and let the chips fall where they may."
Another financial consideration pushing some to sue is the requirement that life insurance payouts be deducted from the compensation amount.
A survivor who received a large insurance payment would still be eligible for the minimum fund amount, $250,000, but may decide that amount is worth giving up in order to fight for answers in court.
After Dec. 22, decisions on the fund will be final.
"Who knows?" Gabrielle said. "Maybe in five or six years, I'll be kicking myself."