Pull up your calendar.

Count the weeks between now and December 31.

Now ask yourself:

What has actually changed in your tax plan since January?

If your income went up, you bought real estate, sold a property, changed jobs, grew your business, or had a much better year than expected — but your tax strategy looks exactly the same — this is the time to look at it.

Because by February or March, much of the conversation becomes:

“Here’s what already happened.”

There is still plenty a CPA can do when preparing the return.

But many of the decisions that shape the return need to happen before the year closes.

Imagine this

You earn $400,000 from your W-2 job.

During the year, you buy a short-term rental.

You’ve heard about cost segregation and bonus depreciation, and you’re expecting a large deduction.

Potentially a great strategy.

But before I get excited about the deduction, I want to know:

Was the property actually placed in service?

How was it rented?

What was the average customer stay?

Did you materially participate?

Who else worked on the property?

Did you keep track of your hours?

Will the resulting loss actually be usable on your return?

Because creating a tax loss and being able to use that tax loss are two different things.

That is what year-end planning is really about.

Here are some of the things I’d review before December 31

1. Is your real estate actually ready for the tax treatment you're expecting?

If you purchased a property this year, simply closing on it does not necessarily mean depreciation starts immediately.

Generally, the property needs to be placed in service — meaning it is ready and available for its intended use.

For a rental, I’d want good documentation showing when that happened.

If you are relying on short-term-rental treatment or material participation, I’d also want to understand the actual activity during the year.

Not a reconstructed story next March.

What actually happened in 2026?

2. Are you documenting your participation now?

This is a big one for real estate investors.

REPS is not simply:

“I got to 750 hours.”

And short-term rentals are not simply:

“I worked more than 100 hours.”

There are multiple rules involved.

For example, Real Estate Professional Status generally involves both a 750-hour requirement and a requirement that more than half of your personal-service time be spent in qualifying real property trades or businesses.

Material participation is a separate analysis.

The important planning point is simpler:

You cannot work additional 2026 hours in March 2027.

And trying to recreate a year's worth of detailed participation after the fact is a much weaker position than maintaining reasonable records as you go.

3. Has your business outgrown its current tax setup?

Maybe January started slowly.

Now you're finishing the year with $250,000, $400,000, or more of business income.

I'd want to revisit things like:

• S-Corp reasonable compensation
• Estimated taxes
• Retirement-plan opportunities
• Reimbursements and accountable-plan expenses
• Equipment or vehicle purchases
• Entity structure
• Whether the books actually reflect what happened during the year

The structure that made sense when you were earning $100,000 may need another look after a much stronger year.

That doesn't mean you automatically change it.

It means you run the numbers again.

4. What needs to happen before year-end?

This is where planning becomes very taxpayer-specific.

Depending on your situation, year-end conversations may include:

• Retirement-plan elections and contributions
• Employee deferrals
• Charitable giving
• Equipment placed in service
• Business expenses and reimbursements
• Capital gains and losses
• Estimated-tax payments
• Real estate purchases and dispositions
• Depreciation strategy
• Paying children legitimately employed in the business
• Income and expense timing

Some items have hard December 31 deadlines.

5. If you have a large loss, what happens next?

This gets overlooked.

People spend a lot of time trying to create deductions.

They spend much less time asking:

What happens if the deduction is bigger than I can use this year?

You may have to consider passive-activity limitations, basis, at-risk rules, capital-loss limitations, or excess-business-loss rules depending on what created the loss.

Sometimes a deduction is usable immediately.

Sometimes it carries forward.

And sometimes the carryforward itself becomes part of next year's planning.

The deduction is only one side of the equation.

The bigger point

The goal isn't to squeeze every possible deduction into the last few weeks of December.

It's to make sure the decisions you're already making line up with the tax result you're expecting.

There is a big difference between:

“What deductions can I still find?”

and:

“Given everything that happened this year, what should I still do before December 31?”

The second question is tax strategy.

And Q4 is one of the best times to ask it.

One other update from Whitestone

We've also given www.whitestonecpa.com a refresh.

The new site better reflects the work we're increasingly doing with real estate professionals and business owners — not just preparing returns, but helping clients think through tax decisions throughout the year.

If you haven't visited in a while, take a look at www.whitestonecpa.com.

And if your tax relationship has mostly been:

“Send everything over after year-end and tell me what I owe,”

this is a good time to have a different conversation.

Waqas “Vic” Hussain, CPA
Whitestone CPA
Based in Chicago. Serving clients nationwide.

If you want a second set of eyes on this before year-end, reply to this email and I'll walk through what I'd want to review in your specific situation.