HomeBlogBlogTax Season Survival Guide: Your Questions, Answered!

Tax Season Survival Guide: Your Questions, Answered!

You asked, we listened! Every year, tax season brings a flood of questions—from filing deadlines and deductions to digital payments and IRS notices. To make things easier, we’ve compiled this clear, concise guide with answers to the most common tax concerns.


Tax Filing & Deadlines

What’s the deadline for filing my tax return?

  • March 15th for S-Corps & Partnerships (1120-S, 1065)
  • April 15th for Individuals (1040) & C-Corps (1120)

If you need extra time, we can file an extension—but keep in mind, this only extends the time to file, not to pay!

What if I owe taxes but can’t pay by April 15th? Yes, but… interest and penalties start accruing after the deadline. If you can’t pay in full, the IRS offers payment plans, and we can help you set one up to minimize fees.


Documents & Filing Process

What documents do I need to send for tax prep?

Make sure you gather:

  • Income docs – W-2s, 1099s, K-1s
  • Expense docs – Receipts, mortgage interest (1098), charitable donations, medical expenses
  • Business docs (if applicable) – Profit & loss, balance sheet, payroll reports
  • Estimated tax payments – Proof of payments made during the year

Missing something? Reach out ASAP so we can help you track it down!

I got a 1099-K from Venmo/PayPal. Do I have to report it? Yes! Even if you don’t receive a 1099-K, all income must be reported, including payments from digital platforms like Venmo, PayPal, and Cash App. If you use these for business, make sure they’re properly recorded in your bookkeeping.


Business Owners & Bookkeeping Questions

What business expenses are deductible? Some commonly tax-deductible business expenses include:

  • Office rent & utilities
  • Software subscriptions
  • Business meals (50% deductible)
  • Mileage & vehicle expenses
  • Continuing education
  • Marketing & advertising

Tip: Not sure if something qualifies? Ask us first—it could save you money!

How do I pay myself as an S-Corp owner? If you own an S-Corp, you must pay yourself a reasonable salary via payroll, which is subject to payroll taxes. Any remaining profit is typically distributed as dividends (not subject to payroll taxes). We can help determine a reasonable salary based on IRS guidelines.

Is S-Corp health insurance taxable? For S-Corp owners with more than 2% ownership, health insurance premiums must be included as taxable income—but they are not subject to FICA taxes. We’ll ensure it’s correctly reported on your W-2.


Common Tax Season Pitfalls & Mistakes

What if I made a mistake on last year’s return? If you find an error or missed deductions from a prior year, we can file an amended return (Form 1040-X) to correct the issue.

I didn’t keep track of my business mileage last year—what should I do? Reconstruct your mileage using:

  • Calendar appointments
  • Google Maps history
  • Credit card receipts for fuel

For 2025 and beyond, start using MileIQ or another tracking app to avoid this headache next year!

Help! I Got an IRS Letter—What Do I Do? First—don’t panic! Many IRS letters are simple requests for information, but some require action. Send it to us ASAP, and we’ll help determine the best course of action.

What if I’m missing a tax document? If a W-2, 1099, or another important document hasn’t arrived, reach out to the issuer first. Still having trouble? Let us know—we can discuss your options, including filing an extension if needed.

Can I still make tax-saving moves for 2024? Yes! You can still contribute to your IRA or HSA before the April 15th deadline, which could lower your tax bill. Need guidance? We can help!


Tracking Refunds & Filing Status

How do I track the status of my refund? Once your return has been filed, check the status through the IRS’s “Where’s My Refund?” tool or your state’s tax website.

Should I file jointly or separately if I’m married? Filing Married Jointly often provides better tax breaks, but Married Separately can be beneficial in cases like:

  • High medical expenses
  • Student loan repayment plans
  • Other financial situations that may require separate filings

We can review your numbers and help you determine the best option.

How does the home office deduction work? If you’re self-employed and use a dedicated home office space, you may qualify for a home office deduction. However, employees working remotely do not qualify under current tax laws. We can help determine if you’re eligible.


Final Reminder

If you haven’t sent in your tax documents yet, don’t wait! The sooner we receive your info, the sooner we can process your return—and the less likely you are to run into filing delays.

Have more questions? We’re here to help—reach out anytime!

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