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Taxes

When a One-Time Rental Sale Triggers an IRMAA Surprise

Jeff Peck  |  May 10, 2026

My understanding is that IRMAA is not permanent. It follows the two-year lookback. A friend and I were discussing the possible sale of his rental property, and that raised the question of what happens if a one-time capital gain pushes someone into a higher Medicare premium bracket.
From what I understand, if someone sells a rental property and has a one-time income spike, that higher income may show up in Medicare premiums two years later, but it should eventually fall back down once a lower-income year becomes the lookback year.

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How Far Behind is the IRS?

Larry Sayler  |  Apr 29, 2026

The IRS still has not processed my mother’s 2024 amended tax return, which they received May 2, 2025.  In a few days, they will have had her return a full year.
My mother submitted her 2024 Form 1040 prior to April 15, 2025.  It said she owed money, so she paid it.  We subsequently found some additional information.  She filed an amended return April 30, 2025.  According to that return, she is due a refund of $2,161. 

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Hidden Surcharge

DAN SMITH  |  Apr 21, 2026

Good Lord, I just turned to AI for a few fun facts. It answered by asking me if my question was in reference to the piece I submitted to HumbleDollar today. While I find that a bit creepy, it gave me an interesting factoid. Here it is, word for word:
The “Hidden Surcharge” Fact: > Most people think the highest marginal tax rate in the U.S. is 37%. However, when you factor in the MAGI “cliff”

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Tax Free Income Trap, Dealing With MAGI

DAN SMITH  |  Apr 21, 2026

It was the first time that Ron’s tax return had a balance due, and he kind of freaked out. On the recommendation of the advisor at his bank, Ron purchased municipal bonds because they were tax exempt. He was shocked to learn that his Social Security benefit became partially taxable. I explained that tax free muni interest was added in with other sources of income to determine if any Social Security income would become taxable. He immediately called his bank person,

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Fixing Social Security once and for all

R Quinn  |  Apr 15, 2026

According to the 2025 Trustee Report, the actuarial deficit for the combined Social Security trust funds under the intermediate assumptions is 3.82 percent of taxable payroll for the 75-year period 2025-99.
We could discuss endlessly how and why we got to this point, but I hope we can agree there is no excuse having had thirty plus years to deal with a coming crisis.
I have a suggestion to get on the right track- take a concept from private pensions.

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Taxes Season 3

Howard Rohleder  |  Apr 11, 2026

This was my third season as an AARP volunteer tax aide…and my third post about my experiences. I volunteer two days a week from February 1 to tax day at two different senior centers which draw from different socioeconomic strata: one is definitely middle class; the other has many clients living on very little.
I began the season wondering how the Big Beautiful Bill would impact our clients. Since most are over 65, I expected the new $6000 senior deduction to have a big,

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Tools/calculators for monthly retirement cash flow and tax estimation

achnk53  |  Apr 9, 2026

We have reached a point now we don’t need to use either free or paid tools or calculators for things like, figure when to claim social security, we have converted all our t-IRA accounts, so no RMD, nor NIIT, nor IRMAA. We have also done our estate planning and a letter of instruction, etc. We did very well with our budgeting with our spreadsheets.  All that is left to figure out annually are our annual retirement cash flow/income,

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Tax Efficiency

Bogdan Sheremeta  |  Apr 4, 2026

TAX EFFICIENT FUND placement is an often underrated topic. The goal of the tax efficient fund placement is to minimize taxes within your investments, and select the right account for those investments.

But how much does that actually matter?

Vanguard’s research finds that a thoughtful asset location strategy can add significantly more value than an equal location strategy. The value added typically ranges from 5 to 30 basis points of after-tax return, depending on circumstances (e.g.,

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Treasury Tax Reporting

Bogdan Sheremeta  |  Mar 28, 2026

IF YOU HAVE a Money Market Fund (e.g. VUSXX, VMFXX), Treasury fund (e.g. SGOV), or any other Treasury ETF (e.g. VBIL), you need to know how to report it on your taxes correctly. If you don’t, you are overpaying on your state taxes unknowingly. 
How and why?
These funds hold U.S. Treasury Bills. Treasuries are exempt from state and local taxes. Of course, this only matters if you hold these funds in a taxable brokerage account,

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Something to Think About

David Lancaster  |  Mar 24, 2026

I have written that for the past few years I have been diligently performing Roth conversions spreading my conversions out on a monthly basis to sort of dollar cost average. In my reading I have learned that when the markets are down it is advantageous to do conversions as when the price goes down you can convert more shares per dollar. With the recent downturns I have been taking advantage of this phenomenon. However I think I may have found an error in my thinking.

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Home Tax Tips

Bogdan Sheremeta  |  Mar 7, 2026

IF YOU OWN a home or are planning to buy one, there are a few things you need to know from the tax standpoint that could save you money:
1. Mortgage Interest
If you have a mortgage, you can typically deduct the interest you pay on the loan up to $750,000 ($1,000,000 if taken before December 16, 2017) but only if you itemize your deductions (schedule A)
You can also deduct points you paid if you itemize.

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Tax Smart Retirement

Adam M. Grossman  |  Mar 7, 2026

A POPULAR JOKE about retirement is that it can be hard work. That’s because financial planning is like a jigsaw puzzle, and retirement often means rearranging the pieces.
In the past, I’ve discussed two key pieces of that puzzle: how to determine a sustainable portfolio withdrawal rate and how to decide on an effective asset allocation. But there’s one more piece of the puzzle to contend with: taxes. Especially if you’re planning to retire on the earlier side,

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A PIN to protect your tax return

Nick Politakis  |  Feb 26, 2026

Have you heard of the IP PIN?
(This is from the IRS website)
“An identity protection PIN (IP PIN) is a six-digit number that prevents someone else from filing a tax return using your Social Security number (SSN) or individual taxpayer identification number (ITIN). The IP PIN is known only to you and the IRS. It helps us verify your identity when you file your electronic or paper tax return.
If you don’t already have an IP PIN,

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What could save Social Security and Medicare or bring it closer to insolvency

Nick Politakis  |  Feb 23, 2026

For those HD readers that want to know about the future of two of our biggest entitlement programs.
A new study from the Cato Institute about who pays more in Social Security and Medicare taxes  than actually receives in benefits that has resulted in a $1.7 trillion benefit to those two programs.  Listen or read the piece on Markeplace.
https://www.marketplace.org/story/2026/02/23/immigrants-reduce-deficits-study-shows

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IRA Flat Tax Proposal

Mark Gardner  |  Feb 18, 2026

David Bach has an interesting whitepaper that proposes the government offer a program where withdrawals from retirement accounts are taxed at 12% from ages 60 to 68. The thesis is that 83% of the boomer generation do not tap into their IRA until RMDs forces them to.
What do you think?

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