Services

Investment & Retirement Taxes

Selling an investment, renting out a property, or starting to draw on retirement savings all change your tax picture, often more than people expect. I prepare your return and help you see the tax result of a decision before you make it.

Who I work with

I work with investors, rental property owners, and people who are retired or getting close. You and your financial advisor choose the investments. I show you what each choice does to your tax bill.

What I help with

  • Capital gains and losses. How a sale is taxed, how long-term and short-term gains differ, and how losses offset gains.
  • Rental property. Rental income and expenses, depreciation, and what happens to that depreciation when you sell.
  • Retirement distributions. How withdrawals from IRAs, 401(k)s, and pensions are taxed, and how to plan the amount you take each year.
  • Required minimum distributions. When they start for you, how much they are, and how they fit with your other income.
  • Social Security. How much of your benefit is taxable, and how other income changes that.
  • Retirement contributions. Whether an IRA, SEP, or other contribution would lower your tax for the year.
  • Withholding and estimated tax. Setting payments so you aren't short in April.

How planning works

Most of these decisions have a deadline at year end, so the useful conversation happens before December. We look at your income for the year, what you're thinking of selling or withdrawing, and how the pieces interact. You see the tax on each option side by side.

Common questions

Is my Social Security taxable?

It depends on your other income. For some people none of it is taxed, and for others up to 85% of the benefit is. Wages, withdrawals, and investment income all count toward that test.

When do I have to start taking required minimum distributions?

The starting age depends on the year you were born, and the rules have changed more than once. I'll confirm your date and the amount, and plan withdrawals around it.

What happens tax-wise when I sell a rental property?

You have a gain or loss on the sale, and the depreciation taken over the years is taxed as part of that gain, some of it at a different rate. Running the numbers before you list the property avoids surprises.

Would a retirement contribution lower my tax this year?

Often, yes, depending on the type of account, your income, and whether you have a plan at work. Some contributions can be made up to the filing deadline, so there's time to decide after the year ends.

If you'd like to talk through your situation, book a free intro meeting. There's no cost and no obligation.

Book a Free Intro Meeting
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Jakubowski Tax Service LLC

Brookfield, Wisconsin

(262) 207-4297 · [email protected]

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