Taxes

I don’t know about your state, but in Ohio, if you drive a hybrid or electronic vehicle, expect to cough up between $100 and $200 extra for license plates, in order to offset the loss of gas tax revenue. Gas tax revenue helps keep our roads in good condition, so it’s only fair that vehicles using less gas, or no gas at all, do their part to maintain the roads.
Even before Henry Ford invented the assembly line,

At the risk of red down arrows, enough complaining about IRMAA and writing about strategies to lower or avoid those premiums.
The median income for retirees age 65+ is $47,000 – $55,000 annually. 
The median HOUSEHOLD income at all ages is about $84,000
IRMAA premiums start at a single person income of $109,000.

If you are retired and required to pay IRMAA premiums, you are doing quite well. As the saying goes,

 
In some situations thousands of tax dollars can be saved by using the married filing separate filing status. However, doing so can trigger a larger income-related monthly adjustment amount (IRMAA) to your Medicare premium.
For example, the monthly adjustment for a single taxpayer with modified adjusted gross income of $109,000 is $81.20 per month. A married taxpayer filing separately with the same income will have a monthly adjustment of $446.30. In that situation it will most likely be better to file a joint tax return and pay the extra income tax.

This discussion (at least the first 2 points) recently came up on the Retirement and IRA Show podcast and I was curious how you all view it.
I suspect most of us view IRMAA on the cost side of the ledger, as either a tax or a fee that is applied, in cliff fashion, to that one extra dollar as defined by our federal government.
The discussion on the show opened my mind to the fact that Medicare has a base cost and unless you are making a ton of income,

BEFORE THE YEAR ENDS, I wanted to cover a great concept – tax-loss harvesting. It’s a strategy to lower your tax liability by selling investments and repurchasing a similar one. The loss can be used to cancel out gains from other investments, which helps reduce the taxes you owe. Or you can use up to $3,000 of those losses each year to lower your taxable income if you don’t have any gains.
Here’s the key goal of the tax-loss harvesting strategy:
Swap assets into similar,

BUSINESS OWNERS HAVE far more control over their tax bill than W-2 employees. But only if you know how the rules actually work. 
The tax code is structured to reward self employment, business investment, and retirement saving, yet many business owners leave significant money on the table simply because they are unaware of all the strategies.
If you are eligible, a Solo 401(k) plan can be an effective way to lower your taxes or shield your investments from future taxation.

THE IRS JUST provided some guidance on how the tips and overtime deductions will work. I wanted to spend a few minutes going over the details so that you can learn how it would be reported on your taxes and share this with friends and family.
Overtime
As a reminder, the OBBBA created Section 225, which allows you to deduct qualified overtime compensation.
This deduction is capped at $12,500 per return ($25,000 for joint filers) and is subject to a phaseout based on modified adjusted gross income.

Today, 12/09/2025, the IRS issued Notice 2026-5 titled “Expanded Availability of Health Savings Accounts under the One, Big, Beautiful)Bill Act (OBBBA)“. This notice should not be confused with the proposed bill that Bogdan wrote about in an earlier Humble Dollar article on 11/27/2025.
The 2026-5 notice provides guidance on changes relating to health savings accounts (HSAs) that were enacted and these changes generally expand the availability of HSAs .
Key points of the notice-
Made permanent a safe harbor for the absence of a deductible for telehealth and other remote care services in existing law.

I am currently trying to convert as much of my wife’s traditional IRA to a Roth. I consider the 12% tax bracket the sweet spot as for every dollar after that the tax nearly doubles to 22%. Earlier this year I calculated what I think is the maximum income one can have for a couple 65+, married, filing jointly with no other complicating additional income, deductions, nor credits, and using the standard deduction. Some terminology may be incorrect.

On 12/02/2025 the IRS issued Notice 2025-68 which is a notice of intent to issue regulations with respect to section 530A Trump accounts that will become active no sooner than July 4, 2026, one year after the signing of the legislation  commonly referred to as OBBBA. Thus the IRS is in the very early stages of the writing of the tax rules as this 44 page notice is not proposed regulations or final regulations but largely a question and answer format of IRS preliminary thinking and intent to propose regulations providing guidance.

WHERE YOU PUT your investments can make a huge difference for your after-tax wealth. 
As you know, we have 3 main investment accounts:

Taxable account. A traditional brokerage account where you are taxed every time you dividends or sell investments at a gain.
Tax deferred account. Traditional 401(k), 403(b), and traditional IRAs allow taxes to be deferred to the future. You pay taxes when your investments are withdrawn, and generally come with an immediate tax deduction.

A new bill was introduced on 11/20 in Congress to amend some HSA rules. It still has to go through the Ways and Means, House and Senate.
I doubt it will get through this year, but it’s good to be aware of potential changes.
If enacted, all the changes would go effective after December 31, 2025, but it’s very unlikely.
In particular, there are 2 main proposals:
> Income limits
> 2 Year rule
Currently, there is no income limitation to contribute to an HSA.

Today, 11/24/2025, I logged into mysocialsecurity.gov account. On the Benefit Verification Letter tab I found my December 2025 benefit amount that will be paid in January 2026. There was currently no indication of my 2026 SS benefit on the main SSA splash page. The gross amount for 2026 was equal to my 2025 gross amount plus the announced 2.8%  COLA as rounded down to the whole dollar. My 2026 Medicare Part B premium deduction was the standard $202.90 per month as previously publicly announced.

SECTION 415(D) OF the IRC requires the Secretary of the Treasury (IRS) to annually adjust limitations for cost-of-living increases. So, let’s dive into some of the changes:
 
401(k), 403(b), and Most 457 Plans:

For 2026, the 401(k)/403(b)/457(b) amount you can contribute is increasing from $23,500 to $24,500. If you are in a 24% marginal tax rate, that’s an additional $240 of federal taxes you can defer. If you are over age 50, the catch-up contributions are also increasing by $500,

MANY PEOPLE ARE familiar with tax loss harvesting, where you sell a losing security/ETF and rebuy a similar, not identical, security/ETF.
But often we don’t really think about the opposite side of the coin: sell a winning security/ETF and rebuy the exact same, or a different, security/ETF.
That strategy is called tax gain harvesting, and because it’s a gain, the wash sale rule doesn’t apply.
 
Execution
Long-term capital gains can be taxed at 0% depending on your income.