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181 Articles

Drew Wood | Jun 26, 2026 at 9:43 AM EDT

The Portfolio That Quietly Pays Your Property Taxes Forever

The mortgage is supposed to be the finish line. Then one day the house is paid off and another realization…

Drew Wood | Jun 25, 2026 at 3:23 PM EDT

The Portfolio That Quietly Pays For Your Midlife Crisis Car

A $1,500 monthly car payment can buy a Porsche 911 lease, a Corvette Stingray note, or a Cadillac Escalade with…

Drew Wood | Jun 25, 2026 at 7:52 AM EDT

Build A Dividend Portfolio That Pays a $2,500 Monthly Mortgage

Most homeowners think of the mortgage as a bill that arrives every month and must be paid. Investors can frame…

Drew Wood | Jun 22, 2026 at 9:09 AM EDT

The Portfolio That Quietly Pays For Your Gasoline Forever

The average American household spent about $200 per month on gasoline according to the latest federal expenditure data. With gasoline…

Drew Wood | Jun 19, 2026 at 4:03 PM EDT

The $1 Million Retirement Mistake: Counting Income You’ll Never Get to Spend

A $1 million portfolio is often discussed as though the balance itself answers the retirement question. It does not. What…

Drew Wood | Jun 19, 2026 at 2:56 PM EDT

The Retirement Portfolio That Forks Over a $10,000 Check Every Month

Ten thousand dollars a month works out to $120,000 a year, an income stream that exceeds the roughly $68,359 in…

Drew Wood | Jun 18, 2026 at 11:34 AM EDT

This $2 Million Portfolio Pays a Six-Figure Income Without Owning a Single Rental Property

A $2 million investment portfolio can generate a six-figure income stream without tenants, maintenance calls, property tax surprises, or vacancy…

Drew Wood | Jun 17, 2026 at 11:54 AM EDT

Why Own Rental Property When Dividend Income Can Pay You $10,000 a Month?

A $10,000 monthly income stream is one reason many investors gravitate toward rental real estate. It promises meaningful cash flow,…

Drew Wood | Jun 17, 2026 at 8:59 AM EDT

How to Build $5,000 a Month in Dividend Income and Never Touch Your Principal

Five thousand dollars a month is the income many retirees are trying to generate from their investments. It is enough to…

Drew Wood | Jun 16, 2026 at 2:49 PM EDT

How to Build $3,000 a Month in Dividend Income to Cover the Average Social Security Check

The average retired worker receives roughly $2,000 a month from Social Security. For many retirees, that covers only part of the…

Drew Wood | Jun 15, 2026 at 11:58 AM EDT

This $1.7 Million Portfolio Pays More Than a Member of Congress

A rank-and-file member of Congress earns $174,000 per year. A dividend portfolio can generate the same level of income without…

Drew Wood | Jun 12, 2026 at 5:19 AM EDT

A $310,000 Portfolio That Pays More Than the Rent on a Big-City East Coast Studio Apartment

Rent for a studio apartment in many major coastal cities, including Seattle, Boston, New York, Miami, Los Angeles, and San…

Drew Wood | Jun 11, 2026 at 7:04 AM EDT

A $480,000 Portfolio That Showers You With $36,000 a Year Without Touching Principal

Thirty-six thousand dollars a year sits at the center of many retirement plans. It is roughly comparable to the annual…

Drew Wood | Jun 10, 2026 at 5:05 AM EDT

A $620,000 Portfolio That Pays More Than the Average Social Worker’s Salary

Healthcare social workers earn roughly $68,000 per year on average in the United States, making them one of the higher-paid…

Drew Wood | Jun 9, 2026 at 5:08 AM EDT

Get Paid Like an Indiana Police Officer With $5,000 a Month in Dividend Income After Taxes

Five thousand dollars a month in spendable dividend income works out to $60,000 per year after federal tax, roughly equivalent…

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Main Street Capital : MAIN

All Main Street Capital Articles

The Portfolio That Quietly Pays Your Property Taxes Forever

The Portfolio That Quietly Pays For Your Midlife Crisis Car

Build A Dividend Portfolio That Pays a $2,500 Monthly Mortgage

The Portfolio That Quietly Pays For Your Gasoline Forever

The $1 Million Retirement Mistake: Counting Income You’ll Never Get to Spend

The Retirement Portfolio That Forks Over a $10,000 Check Every Month

This $2 Million Portfolio Pays a Six-Figure Income Without Owning a Single Rental Property

Why Own Rental Property When Dividend Income Can Pay You $10,000 a Month?

How to Build $5,000 a Month in Dividend Income and Never Touch Your Principal

How to Build $3,000 a Month in Dividend Income to Cover the Average Social Security Check

This $1.7 Million Portfolio Pays More Than a Member of Congress

A $310,000 Portfolio That Pays More Than the Rent on a Big-City East Coast Studio Apartment

A $480,000 Portfolio That Showers You With $36,000 a Year Without Touching Principal

A $620,000 Portfolio That Pays More Than the Average Social Worker’s Salary

Get Paid Like an Indiana Police Officer With $5,000 a Month in Dividend Income After Taxes

What Will It Take for XRP to Break Through $2?

Her Annuity Pays $1,580 a Month, Guaranteed for Life. At 73, It Pushed Her Medicare Premium Up Two Brackets.

The Fire Closed His Photography Studio at 63. Social Security Counted the Canceled Weddings, Not the Burned Cameras.

Her Annuity Pays $1,580 a Month, Guaranteed for Life. At 73, It Pushed Her Medicare Premium Up Two Brackets.

The Fire Closed His Photography Studio at 63. Social Security Counted the Canceled Weddings, Not the Burned Cameras.

What Will It Take for XRP to Break Through $2?

Her Annuity Pays $1,580 a Month, Guaranteed for Life. At 73, It Pushed Her Medicare Premium Up Two Brackets.

Main Street Capital : MAIN

All Main Street Capital Articles

The Portfolio That Quietly Pays Your Property Taxes Forever

The Portfolio That Quietly Pays For Your Midlife Crisis Car

Build A Dividend Portfolio That Pays a $2,500 Monthly Mortgage

The Portfolio That Quietly Pays For Your Gasoline Forever

The $1 Million Retirement Mistake: Counting Income You’ll Never Get to Spend

The Retirement Portfolio That Forks Over a $10,000 Check Every Month

This $2 Million Portfolio Pays a Six-Figure Income Without Owning a Single Rental Property

Why Own Rental Property When Dividend Income Can Pay You $10,000 a Month?

How to Build $5,000 a Month in Dividend Income and Never Touch Your Principal

How to Build $3,000 a Month in Dividend Income to Cover the Average Social Security Check

This $1.7 Million Portfolio Pays More Than a Member of Congress

A $310,000 Portfolio That Pays More Than the Rent on a Big-City East Coast Studio Apartment

A $480,000 Portfolio That Showers You With $36,000 a Year Without Touching Principal

A $620,000 Portfolio That Pays More Than the Average Social Worker’s Salary

Get Paid Like an Indiana Police Officer With $5,000 a Month in Dividend Income After Taxes

What Will It Take for XRP to Break Through $2?

Her Annuity Pays $1,580 a Month, Guaranteed for Life. At 73, It Pushed Her Medicare Premium Up Two Brackets.

The Fire Closed His Photography Studio at 63. Social Security Counted the Canceled Weddings, Not the Burned Cameras.

Featured Reads

Her Annuity Pays $1,580 a Month, Guaranteed for Life. At 73, It Pushed Her Medicare Premium Up Two Brackets.

The Fire Closed His Photography Studio at 63. Social Security Counted the Canceled Weddings, Not the Burned Cameras.