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We have four houses worth $6 million plus stocks and collectibles worth millions more. Do we get a long-term care policy or pay it out of pocket?

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We have four houses worth $6 million plus stocks and collectibles worth millions more. Do we get a long-term care policy or pay it out of pocket?

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I’m 47, left my job and want to convert my $130,000 traditional IRA to a Roth. What’s the best tax strategy? 

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We’re in our 70s, have $1.3 million in IRAs and $1.15 million in cash. But we have ‘no clue’ what to do with the money. 

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My wife and I plan to retire at different times. How do we find our ‘magic’ retirement number? 

The latest Help Me Retire columns from MarketWatch.

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I’m 72, have $3 million in savings, and want to live with my son when he’s married with children. Can I afford two apartments?

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‘I’m hoping to remain in my home’: I’m 76 with no relatives. What should I do with my estate?

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My husband and I are in our 50s. Large-cap ETFs seem expensive. Does it make sense to add them to our retirement accounts?

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My wife and I are approaching 60 and have 10-year-old twins. We don’t have 529 plans. How can we retire with looming college costs? 

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We’re in our 50s and have free housing — for now. Should we save for retirement or buy a house?

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Reverse mortgage, sell the house or Medicaid? How can my parents pay for long-term care?

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Should I claim Social Security — or wait and live off my 401(k)? How do I make this decision?

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I have about $3 million in pension and savings. Should I claim Social Security earlier than 70?

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I want to retire at 55 in a country with free health care. My spouse will draw Social Security, and I have $160,000. Are we crazy?

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‘Nobody ever told me’: How do I make sense of Social Security Disability Income & Veteran’s benefits? Please help.

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I’m 56 and have $3.4 million in assets. I’m semi-retired, but my spouse, 64, has no savings. How do we move forward?

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I’m 76 with $73,000 in an investment account that has not increased in 2 years. Should I abandon the 50/50 strategy?

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Meta’s stock soars toward record on first-ever dividend — but Zuckerberg sees ‘unpredictable and volatile’ years ahead

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Amazon’s big earnings beat and upbeat cloud talk send its stock soaring

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Meta stuns Wall Street with its first dividend. Amazon and Alphabet could be next.

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How to start planning for your retirement as a teenager

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My wife and I sold our home to her son at a $100,000 discount. He’s now selling at a $250,000 profit. Do I ask for a cut?

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My brothers are co-owners of our ailing mother’s accounts worth $1.9 million. I’m listed on a $100,000 brokerage account. How can I rectify this?

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I’m 73. Should I cash my $150,000 IRA and $80,000 brokerage account — and wait for the market to crash?

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Mortgage rates dip after Fed meeting. Freddie Mac expects rates to decline more.

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How to spot a deepfake

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Medical-device makers’ stocks jump as procedures keep going strong

More from Help Me Retire

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We’re retired with $1.4 million in investments and two mortgages worth $200,000. Do we pay them off and risk raising our Medicare premium? 

Dec. 29, 2023 at 5:57 a.m. ET by Alessandra Malito
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I’m 62 and single with a ‘mountain of debt,’ and a desire to start a business. Am I in a position to take a financial risk?

Dec. 27, 2023 at 5:45 a.m. ET by Alessandra Malito
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I’m 64, make $1,500 a month driving Uber and get almost $5,000 a month in pensions and Social Security — should I pay off my mortgage before I retire?

Dec. 23, 2023 at 12:57 p.m. ET by Alessandra Malito
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We’re in our 70s with a chronic illness. We have $300,000 in 6-month CDs, and $100,000 in cash. Are we on the right track?

Dec. 20, 2023 at 5:07 a.m. ET by Alessandra Malito
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‘We stay in two-star hotels’: We’re 70 and have $1.8 million, but my husband insists on living cheap. Don’t we have enough?

Dec. 16, 2023 at 1:09 p.m. ET by Alessandra Malito
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I’m 59 and have $190,000 in income in quasi-retirement. Can my wife and I live comfortably with one or two trips a year? 

Dec. 16, 2023 at 7:00 a.m. ET by Alessandra Malito
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I’m 71 and can’t decide if I should pay off my mortgage or get a joint annuity that’s cheaper — what should I do?

Dec. 11, 2023 at 11:05 a.m. ET by Alessandra Malito
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My husband says we’ll be ‘homeless’ if we keep renting. We’re 68 and 74 — do we buy a home instead?

Dec. 9, 2023 at 3:00 p.m. ET by Alessandra Malito
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We have $3 million in real estate, which brings in $70,000 a year. Could I make the same income investing in stocks and bonds? 

Dec. 9, 2023 at 7:05 a.m. ET by Alessandra Malito
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I’m 60 with $6,100-a-month in Social Security disability and a pension. I want my money to work for 20 years — what do you recommend?

Dec. 2, 2023 at 7:20 p.m. ET by Alessandra Malito
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I’m 67 and retired with $57,000 left on my mortgage and $600,000 saved for retirement — should I pay off my home now?

Dec. 2, 2023 at 7:03 p.m. ET by Alessandra Malito
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I’m 53 and hate my job. My husband, 59, and I have two homes, plus $1 million in savings. Can we afford to retire?

Dec. 2, 2023 at 1:46 p.m. ET by Alessandra Malito
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Will our Social Security checks be reduced? My wife has a school pension and I’m a veteran.

Nov. 28, 2023 at 12:10 p.m. ET by Alessandra Malito
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I live in a care home, and the costs are overwhelming. How can I qualify for Medicaid without spending down all my assets?

Nov. 27, 2023 at 9:07 a.m. ET by Alessandra Malito
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What’s the best free online retirement calculator? And how do you plan for all possible outcomes?

Nov. 21, 2023 at 10:35 a.m. ET by Alessandra Malito
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Can my brother get Social Security disability and still pay into a retirement account? ‘He recently developed a severe medical problem.’

Nov. 19, 2023 at 12:59 p.m. ET by Alessandra Malito
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‘I wake up with anxiety’: My husband leaves retirement-investing plans to me. How do I hire the right adviser?

Nov. 18, 2023 at 7:41 p.m. ET by Alessandra Malito
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I’m 64 and was forced into retirement. Should I convert my $1.3 million to a Roth IRA? 

Nov. 4, 2023 at 10:58 a.m. ET by Alessandra Malito
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I want to invest $100,000 in dividend-paying stocks, but my wife doesn’t. How do I convince her? 

Oct. 28, 2023 at 3:44 p.m. ET by Alessandra Malito
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I’m 92 and will probably live to be 100. I have about $250,000. Thoughts?

Oct. 23, 2023 at 2:26 p.m. ET by Alessandra Malito