ELIZABETH wanted help selling her husband’s house to contribute toward his care. George had moved to an assisted living facility about a year earlier. Elizabeth was living with her daughter, so George’s empty house had fallen into disrepair.

We listed the house, which had a mortgage balance of $190,000, for $325,000, but we soon learned that George had refinanced the house, adding $100,000 in debt. A buyer offered $330,000 but wanted nearly $10,000 in closing costs. The inspection revealed damage, prompting the buyer to ask for a $5,000 price cut. Then an $8,000 credit card debt popped up. Elizabeth would have had to pay $3,000 to close the sale.

I started negotiating. First, the credit card debt came down. Then the buyer lowered the repair costs to $2,500. I cut my commission by $1,500, and the buyer’s agent reduced her fee by $500. Elizabeth walked away with only $800 or so, but she avoided more expenses or foreclosure. —Tabitha Richardson, real estate broker, Maryland, Virginia and Washington, D.C.

PRO TIP: When you sell a house, always be prepared for additional expense, from repairs to closing costs. But keep in mind that everything—absolutely everything—is negotiable.

CLARA, 82, had never received a Social Security check despite contributing to the program since 1970. She had applied late, mistakenly believing that the monthly benefit based on her work record would continue to grow until she turned 72. (It stops growing at 70.)

An even bigger problem was that when Clara, an immigrant, submitted her initial application to the Social Security Administration (SSA), she had lost the certificate of naturalization proving she was a U.S. citizen. She requested a copy from the federal Citizenship and Immigration Services agency (USCIS), but the copy never arrived. Nine years later, in 2023, her daughter found her original certificate in a storage box. She and her mother hand-delivered it to her local SSA office. Yet Clara, 81 at the time and facing financial difficulties, received no benefit. Her children then contacted my company.

We identified a rule requiring the SSA to assist claimants in obtaining evidence of eligibility from other federal agencies. Clara had retained all the paperwork showing the SSA had never helped her with the unresponsive USCIS, so we drafted the necessary paperwork to compel the SSA to quickly address this issue. In March of this year, Clara recovered $270,325.60 and was approved for an ongoing monthly benefit of $3,336. —Matthew Allen, CEO of Social Security Advisors, New York City

PRO TIP: There are thousands of rules in the Social Security system. The average person doesn’t know even three of them. And miscalculations and other errors on the part of the SSA are common. So document all your interactions with the SSA. In tricky situations like this one, it may help to consult a professional.

JEN AND DAVID, both in their 60s, lived in a $4 million house outside Philadelphia, drove luxury cars and belonged to multiple country clubs. But David, a high-level executive, maintained a secret life with another woman. Once Jen discovered this, she wanted a divorce.

The problem for Jen was that she had no knowledge of their investments, their net worth or how much money David made. She had given up her job early in their marriage to care for their two children, now adults, and David had always kept her on an allowance. She had access to checking and savings accounts at their local bank, but that was it.

So I assisted Jen in meeting with an attorney and initiating discovery, a formal legal process to investigate assets, debts and other relevant information. We soon learned that David had purchased a house for his mistress. We also learned that he had substantial deferred compensation—money he was guaranteed to receive in the future, which Jen might be entitled to but that wouldn’t show up if you were just looking at the couple’s current assets. The big shocker: The couple’s net worth was about $30 million more than Jen had realized.

Eventually, the court determined Jen was entitled to more than half of the couple’s assets. David also agreed to maintain life insurance to cover alimony obligations. —Christine Palmer Hennigan, financial adviser and certified divorce financial analyst, West Chester, Pennsylvania

PRO TIP: Be prepared for the business side of divorce by getting a clear picture of your financial situation. Track your spending to document your standard of living; that’s important in determining any future alimony payments. Build a balance sheet listing all your properties, investments, and other assets and debts. Your insurance coverage and your tax return will help shed light on what you own.

DESPITE making no changes to their property and never filing a claim, Betty and Don, retirees in a $1.1 million house near Lake Tahoe, were dropped by their insurer. Under current California rules, the insurer could not properly underwrite and price the policy to cover the area’s increased fire risk.

I explained that to maintain similar coverage, they would have to replace their old $1,800 annual policy with two new ones. The first would cover everything but fire damage for $3,100 annually. For fire coverage, they would have to use California’s FAIR plan (which stands for “fair access to insurance requirements”). More than 30 states offer last-resort policies providing basic coverage for properties exposed to high risks, typically from natural disasters. But the FAIR premium cost was still high: $6,800 for the couple’s 2,000-square-foot home.

To cut their premiums, we raised the deductible to $10,000 on the residential policy and to $15,000 on the FAIR policy. Next, we lowered the coverage of personal property on both policies from $700,000 to $150,000, removed coverage for an additional shed-like structure, and eliminated coverage for the cost of temporary housing if damage forced them from their home. That cut their total premiums to about $6,000, down from nearly $10,000. It’s still a lot more than they were paying, and their coverage is lower, but they are protected. —Karl D. Susman, insurance broker, Los Angeles

PRO TIP: Don’t compare past insurance options with current ones. Today you may need to either reduce your coverage or pay higher premiums. There are steps you can take, however, to reduce the likelihood of property loss—such as installing a noncombustible roof, covering the eaves to prevent embers from getting underneath, and clearing brush from around your house—that may help lower your premium.

OVER FOUR years, Eduardo, a scientist, had claimed $100,000 in business losses related to work he had conducted in his spare time on chemicals to be used in the production of art. By the fifth year, he had developed a marketable chemical and began to make a profit.

The IRS categorized his work as a hobby, disallowing the $100,000 in losses and leaving Eduardo liable for back taxes and penalties. They deemed it a hobby partly because Eduardo had a full-time job and his side gig hadn’t shown a profit.

To establish Eduardo’s business status, we helped him set up a limited liability company, which typically costs $1,000 or less. We reviewed his records for the past five years and produced periodic financial statements. The IRS was persuaded that Eduardo had a business and let him claim the losses. —Steven M. Packer, senior manager, Tax Accounting Group, Duane Morris, Philadelphia

PRO TIP: The IRS generally requires profits in three out of five consecutive years for an activity to qualify as a business. It’s essential to retain all receipts, keep accurate records, and have a separate bank account for business income and expenses.

CHRISTINE, a busy executive working in New York City, hired us to investigate why her elderly mother, Agnes, was running out of funds every month in her checking account. Agnes’ expenses were minimal: utilities, groceries, costs for her two cats and some medical bills—all of which she could cover with her monthly Social Security check. Christine owned the upstate New York house where Agnes lived, and she paid Julie, Agnes’ full-time caregiver, along with the property taxes and insurance.

When we took over the account and imported the data into Quicken, we discovered it was overdrawn and that seven checks had bounced in a two-month period, including some to collection agencies. We also found that eight credit card accounts had been opened relatively quickly, with small payment checks written out to the card companies. Agnes, who had MS, could barely sign her name, and Julie was filling out the checks. We alerted Christine, who used her power of attorney to obtain copies of the credit card applications, confirming Julie’s involvement.

At this point, the debt was close to $69,000. Christine consulted an attorney, who said there was sufficient evidence to prosecute Julie. But Agnes, who loved Julie, refused to pursue legal action—and wanted to keep her on. Christine’s brother eventually took over daily money management, and Julie was required to provide receipts for all expenses. —Keeley Kriskey, daily money manager with Financial Sense in Darien, Connecticut

PRO TIP: Place a freeze on your loved one’s accounts with the three main credit bureaus, so no one can open a new credit line in their name. Also, set up online access to their financial accounts, so you can monitor activity and request fraud alerts.

UPON retirement, Nancy left her small business to her daughter Amy. A year later, Nancy started getting calls from the issuer of the company’s credit card; her Social Security number was still on the account. It turned out that the business was $50,000 in debt and on the brink of collapse.

Nancy couldn’t afford to pay off the debt. Since her account had fallen delinquent and her credit rating had plunged, she couldn’t get a bank loan or transfer the balance to another card. But as a nonprofit credit counseling agency, we negotiated with her creditor to lower the interest rate on the debt to under 2 percent, cutting her payments from $1,400 a month to $700. We also advised Nancy to return to work part-time, which she did. Today she is doing well. —Lara Ceccarelli, credit counselor, American Financial Solutions, Bremerton, Washington

PRO TIP: Communicate with family members or anyone who has the ability to affect your credit rating. If you encounter financial problems, seek help to negotiate better terms.

A FAMILY approached us during their daughter Sarah’s senior year of high school. They had no college savings. Sarah’s top choice was Boston University. But based on her parents’ finances, she wouldn’t qualify for need-based aid. That meant she would have to fund B.U.’s total cost of roughly $350,000 through loans.

Sometimes the emotional aspect of choosing a college keeps people from considering the long-term financial consequences. So we did the math to help it all sink in. For every $10,000 Sarah borrowed, she should expect a $100 monthly payment. With loans that could top $300,000, she might have a monthly payment of at least $3,000. Meanwhile, an average starting salary is about $5,000 a month. You hate to see a 17-year-old who has barely gotten a driver’s license start life with that much debt.

We showed Sarah how other colleges on her list were more affordable. Ultimately, she chose a different school, with an annual cost of around $35,000. —Andrew Holmes, financial planner specializing in college funding, Newton, Massachusetts

PRO TIP: Begin the college selection process early, and focus on schools offering generous need-based or merit-based aid. Prestigious schools may be enticing, but you can get an excellent education at a place that aligns with your financial resources.

Karen Cheney is a personal finance journalist who has written for Money and other publications.