Facing Tax Challenges Head-On: Common Issues and Smart Solutions

Last year, a local contractor filed his taxes without realizing a 1099 form hadn’t been issued until weeks later. The result? A mismatch triggered an IRS notice and a wave of anxiety. Fortunately, the issue was resolved quickly—but only because he acted fast and had the right support.

Tax season can be overwhelming, especially for individuals and small business owners navigating back taxes, IRS notices, and complex financial records. According to the IRS, millions of returns are filed with errors every year. These missteps often trigger additional scrutiny, financial penalties, or delays in refunds.

Understanding common tax problems—and knowing how to address them—can reduce stress and help you stay on solid financial ground.

Misreporting Income and Expenses

Accurate tax reporting is essential to avoid red flags with the IRS. Yet, one of the most frequent issues individuals and businesses face is misreporting income or failing to include forms like 1099s, K-1s, or W-2s.

How to Avoid Misreporting

• Maintain year-round records of all income, including freelance, investment, and rental earnings

• Use bookkeeping software that integrates with bank accounts to reduce human error

• Compare your return against IRS transcripts when available

For business owners, blurring the lines between personal and business expenses is a frequent pitfall. Keep receipts and clear documentation for any deductions you plan to claim.

If a forgotten 1099 or amended form arrives after filing, it can be handled—but swift action matters. Learn how to respond with this helpful article.

Missing Tax Deadlines or Payments

Late filing or missed payments are common triggers for IRS penalties and interest. Even if you apply for a filing extension, it doesn’t extend your deadline to pay.

Tips for Staying on Schedule

• Add tax filing and payment dates to a shared calendar

• Set reminders 7-10 days before each due date

• Consider automatic scheduling of estimated tax payments if self-employed

If a deadline slips by, filing and paying as soon as possible can help reduce additional penalties. For larger debts, the IRS offers installment options—but timely coordination is key.

Overlooking Tax Deductions and Credits

Every year, taxpayers leave money on the table. Whether it’s due to lack of awareness or unclear guidance, many miss deductions and credits that could significantly reduce their tax burden.

Frequently Missed Deductions

• Home office expenses

• Health Savings Account (HSA) contributions

• Self-employed retirement plan contributions

Valuable Tax Credits to Review

• Child and dependent care credit

• American Opportunity and Lifetime Learning education credits

• Energy-efficient home improvement credits

Proper tax preparation ensures these opportunities are reviewed and applied where eligible, especially if your income, family size, or business status has changed. For support with individual filings, explore personal tax preparation services from Gregg Jaffe.

Navigating Small Business and Self-Employment Taxes

Self-employed individuals and small business owners often face additional tax challenges—from estimated quarterly taxes to payroll filings and business entity selection.

Key Tips for Business Owners

• Select a structure (LLC, S-corp, sole proprietorship) that aligns with tax planning goals

• Keep separate accounts and credit cards for business use

• Stay current with 1099 filings, payroll submissions, and sales tax requirements

Partnering with a tax professional for ongoing planning helps manage cash flow, minimize liabilities, and avoid year-end surprises.

Dealing with IRS Notices and Audits

Receiving a letter from the IRS can cause anxiety, but not all notices signal an audit. Many are requests for clarification, missing documentation, or updated figures.

How to Handle an IRS Notice

1. Read the entire notice carefully—don’t ignore it

2. Verify the details against your own tax records

3. Respond within the timeframe indicated, including supporting documents

4. Contact Gregg Jaffe Tax Services at 516-770-5305 for help interpreting or addressing the notice

   
   

Prompt and professional responses often resolve issues efficiently, minimizing disruption and financial consequences.

Resolve Your Tax Issues with Confidence

Tax issues don’t resolve themselves—but they don’t have to derail your future either. With clear steps and experienced support, you can take control of your situation.

Start with a few practical steps:

• Organize tax documents and prior returns

• Review any recent IRS letters or payment schedules

• Reach out for support if you're unsure about your next move

Whether you’re dealing with a specific tax problem or simply want to avoid one, Gregg Jaffe provides trusted guidance in tax preparation, small business planning, and IRS representation.

Phone: 516-770-5305

Contact Form: https://www.greggjaffetax.com/contact