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BOCA RATON · UPDATED MAY 2026
Quick Answers
Short answers to the questions we get asked most often. If your situation is more nuanced than these answers account for, call us — the initial consultation is always free.
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How long should I keep my tax records?
Tax returns: forever. Supporting documents (W-2s, 1099s, receipts): 7 years. See our full Record Retention Guide for edge cases.
I got an IRS letter. What should I do?
Don't ignore it, and don't call the IRS before calling us. Most IRS letters are routine requests for information. A few require fast, specific action. Bring or email the letter and we'll tell you exactly what it means and what to do.
Should I file an extension?
If you can't file by April 15, yes — file Form 4868 to extend to October 15. But note: an extension is only an extension to FILE, not to PAY. If you owe tax, you still need to pay by April 15 to avoid penalties + interest on the unpaid balance.
Should I make quarterly estimated payments?
If you're self-employed, have significant investment income, or had a large tax bill last year, probably yes. The IRS charges an underpayment penalty if you don't pay enough during the year. Safe harbor: pay 90% of current-year tax OR 100% of prior-year tax (110% if AGI > $150K).
My side gig made $5K last year. Do I need to report it?
Yes. Self-employment income is reportable regardless of whether you got a 1099 — the $600 1099 threshold is about the payer's reporting obligation, not yours. Net self-employment income over $400 also triggers self-employment tax.
Can I deduct my home office?
If you use a specific area of your home regularly and exclusively for business, yes. The simplified method: $5/sq ft up to 300 sq ft ($1,500 max). The actual-expense method: a percentage of actual home costs. For most W-2 employees, the home-office deduction is no longer available (Tax Cuts and Jobs Act rules).
Should I form an LLC or S-Corp?
Depends on your income and goals. An LLC is simpler but pays SE tax on all profit. An S-Corp can save significant SE tax above ~$60-70K net income but requires payroll and formalities. We run the numbers for your specific situation during new-business-formation engagements.
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