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Unlocking the HSA: A Rare Triple Tax Break for Medical and Retirement Planning

Finance Tips, Financial Planning, Health Insurance, Health Savings Accounts, Healthcare, Medical Expenses, Tax Tips
Article Highlights: What is the Purpose of an HSA? Who Qualifies to Contribute? The Tax Benefits of an HSA Maximum Contributions Distribution Issues and Taxation Why an HSA Can also Function as a Retirement Account What…
October 15, 2026
https://www.islernw.com/wp-content/uploads/2026/10/Blog-header-image-unlocking-the-hsa-the-triple-threat-tax-break-Isler-NW-Oregon.png 320 846 IslerNW https://www.islernw.com/wp-content/uploads/2013/12/header_logo_trans.png IslerNW2026-10-15 12:00:342026-10-03 17:02:26Unlocking the HSA: A Rare Triple Tax Break for Medical and Retirement Planning

Don’t Wait Until the Last Minute: October 15 Is the Extended Due Date for 2025 Individual Tax Returns

2026 Due Dates, 2026 Taxes
If you filed an extension for your 2025 individual income tax return, remember that the extended due date is October 15, 2026. That is the deadline to file Form 1040 or Form 1040-SR if you requested an automatic 6-month extension. There are…
October 8, 2026
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Prediction Markets Are Becoming a Tax Issue—Here’s Why That Matters

Investment, Stocks, Tax News
Prediction markets have grown rapidly over the past few years, attracting investors, cryptocurrency enthusiasts, and high-net-worth individuals looking for new ways to participate in financial markets. Platforms such as Kalshi have introduced…
October 8, 2026
https://www.islernw.com/wp-content/uploads/2026/10/Blog-header-image-investment-prediction-markets-and-why-they-matter-state-rules-Isler-NW-Oregon.png 320 846 IslerNW https://www.islernw.com/wp-content/uploads/2013/12/header_logo_trans.png IslerNW2026-10-08 12:00:032026-10-17 17:24:11Prediction Markets Are Becoming a Tax Issue—Here’s Why That Matters

Important October 2026 Individual and Business Due Dates

2026 Due Dates, 2026 Taxes, Taxes
October 2026 Individual Due Dates October 13 - Report Tips to Employer If you are an employee who works for tips and received more than $20 in tips during September, you are required to report them to your employer no later than October 13.…
October 6, 2026
https://www.islernw.com/wp-content/uploads/2026/10/Blog-header-image-important-2026-tax-due-dates-individuals-and-businesses-Isler-NW-Oregon.png 320 846 IslerNW https://www.islernw.com/wp-content/uploads/2013/12/header_logo_trans.png IslerNW2026-10-06 12:00:552026-10-03 17:15:41Important October 2026 Individual and Business Due Dates

Pay Off Debt or Invest? How Higher Interest Rates Change the Math

Debt, Finance, Finance Tips, Financial Planning, Investment
For years, the answer seemed straightforward. Interest rates were historically low, stock markets generally rewarded long-term investors, and many financial experts encouraged people to invest extra money rather than aggressively paying down…
October 2, 2026
https://www.islernw.com/wp-content/uploads/2026/10/Blog-header-image-should-you-pay-off-debt-or-invest-Isler-NW-Oregon.png 320 846 IslerNW https://www.islernw.com/wp-content/uploads/2013/12/header_logo_trans.png IslerNW2026-10-02 12:00:132026-10-03 17:02:54Pay Off Debt or Invest? How Higher Interest Rates Change the Math

Game, Set, Tax: The Parent’s Playbook for Sports Expenses, Deductions, and NIL

Deductions, Tax Credits, Tax Planning, Tax Tips, Taxes
Article Highlights: Sports Expenses As a Childcare Expense Charitable Contributions Volunteering Parents Use of an Asset by a Charity Medical Expense Exception When a Child’s Sport Becomes a Business Recordkeeping…
September 30, 2026
https://www.islernw.com/wp-content/uploads/2026/09/Blog-header-image-Game-Set-Tax-The-Parents-Playbook-for-sports-Expenses-deductions-and-NIL-Isler-NW-Oregon.png 320 846 IslerNW https://www.islernw.com/wp-content/uploads/2013/12/header_logo_trans.png IslerNW2026-09-30 12:00:382026-10-03 16:40:38Game, Set, Tax: The Parent’s Playbook for Sports Expenses, Deductions, and NIL

The Tax Law Changed. The Real Story Is What Comes Next.

Tax Credits, Tax News, Tax Planning, Tax Reform, Taxes
When Congress passes a major tax bill, most people assume the hard part is over. In reality, that's often when the next phase begins. Earlier this month, the U.S. Department of the Treasury and the Internal Revenue Service released their 2026…
September 23, 2026
https://www.islernw.com/wp-content/uploads/2026/09/Blog-header-image-The-Tax-Law-Changed-The-Real-Story-Is-What-Comes-Next-Isler-NW-Oregon.png 320 846 IslerNW https://www.islernw.com/wp-content/uploads/2013/12/header_logo_trans.png IslerNW2026-09-23 12:00:422026-10-03 16:40:09The Tax Law Changed. The Real Story Is What Comes Next.

What Counts as Taxable Income? You Might Be Surprised.

Inheritance, Interest, Tax Planning, Tax Tips, Taxes
Article Highlights: A Simple Example, Finding Money On The Street What Section 61 Is Designed To Do The Basic Idea: Accession To Wealth What Is Usually Taxable? What Is Usually Not Taxable? The General Welfare Exclusion …
September 17, 2026
https://www.islernw.com/wp-content/uploads/2026/09/Blog-header-image-What-Counts-as-Taxable-Income-you-Might-Be-Surprised-Isler-NW-Oregon.png 320 846 IslerNW https://www.islernw.com/wp-content/uploads/2013/12/header_logo_trans.png IslerNW2026-09-17 12:00:322026-09-12 19:46:26What Counts as Taxable Income? You Might Be Surprised.

The Holiday Rush Starts Now: 7 Financial Moves Businesses Should Make Before Q4

Business, Business Development, Entrepeneurship, Financial Planning, Small Business
Retailers are placing inventory orders. Restaurants are planning for seasonal demand. Contractors are scheduling projects before winter. Professional service firms are setting revenue goals they hope to achieve before year-end. Whether your…
September 15, 2026
https://www.islernw.com/wp-content/uploads/2026/09/Blog-header-image-financial-moves-you-should-make-in-q4-for-your-business-Isler-NW-Oregon.png 320 846 IslerNW https://www.islernw.com/wp-content/uploads/2013/12/header_logo_trans.png IslerNW2026-09-15 12:00:372026-09-12 19:47:11The Holiday Rush Starts Now: 7 Financial Moves Businesses Should Make Before Q4

September 15 Is the Third Quarter Estimated Tax Deadline

2026 Due Dates, 2026 Taxes, Personal Finance, Self-Employment, Small Business, Tax Planning, Tax Tips
If you make or receive income that is not fully covered by withholding, September 15, 2026 is an important date on the tax calendar. It is the due date for the third installment of 2026 federal estimated tax payments for individuals who are…
September 12, 2026
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Isler Northwest LLC | 1300 SW 5th Ave #2600, Portland, OR 97201 | 503-224-5321 | Site by Kistner Group | Review us on Google! | Review us on Yelp!
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