Two years later, the state increased the governor’s term to four years, and the Clintons’ finances appeared more stable. Mrs. Clinton went on to join the board of Walmart, and she continued to work at the Rose Law Firm. By the time Mr. Clinton was running for president, they reported $297,177 in total income on their 1992 tax returns, a sum that would put most Americans in the upper income tier but seemed meager compared with the wealth of his opponents, George Bush and Ross Perot.

“When we moved into the White House, we had the lowest net worth of any family since Harry Truman,” Mr. Clinton has said.

The White House years offered a respite from financial worry. As first lady, Mrs. Clinton wrote a book, “It Takes a Village,’’ for which she did not accept an advance and donated the proceeds to charity. “HRC insists she will have time, wants it to have impact (of course, also wants it to make huge bucks),” Mrs. Blair wrote at the time.

Still, the couple’s earlier financial decisions resurfaced in damaging ways. What started as an investigation into the Whitewater investment spun into revelations of Mr. Clinton’s relationship with a White House intern, which led to the president’s impeachment by the House of Representatives.

When the Clintons left the White House after the 2000 election — the first time they were without the safety net of public office in 18 years — they owed $5 million in legal fees and once again felt financial uncertainty. In 2014, Mrs. Clinton described her family’s situation at the time in words that have bedeviled her candidacy: “Dead broke.”

Once again, the Clintons needed a house, and once again they turned to the help of a wealthy friend. This time it was Terry McAuliffe, a longtime Clinton campaign fund-raiser, who offered to guarantee the mortgage on the home they would move into after leaving the White House.

But this time, the home — a $1.7 million, 11-room Dutch Colonial in Chappaqua, a rich suburb — was not one of the smallest houses on the block. Mrs. Clinton did not have to call the Roto-Rooter every time the old pipes clogged or run to a neighbor’s house to borrow milk and eggs, as she had done in the house on Midland Street.

And now it was Mrs. Clinton, eyeing a Senate seat from New York, who left her husband at home as she hit the road, crisscrossing the state for her campaign.