Small Business Tax Strategies

As an S corporation owner, you can avoid the double taxation that plagues income earned by a regular C corporation. Instead of being taxed twice—once on the corporation level and once personally—income flows through to the S corporation shareholders. So, it’s only taxed once at your personal level.

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It took many years, but self-employed people are now even-steven with other business entities when it comes to deducting health insurance. They can write off 100 percent of their health insurance premiums, including amounts paid for family coverage, up to the business’s amount of net income.

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If you offer employees a tax-advantaged flexible spending account (FSA) program, the IRS recently said you can give them an extra 21/2-month "grace period" beyond the plan year to spend their FSA dollars.

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When you started your small business, you poured most of your earnings back into the operation. Unfortunately, that didn’t leave much cash for retirement savings. Now that your business is running smoothly, you may hope to make up for lost ground—and fast.

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Q: My bank told me that it reports any cash deposits above $10,000 to the IRS. But that money doesn’t represent taxable income from a job or an investment; it’s nobody’s business but my own. Does the bank have to report that? J.H., Plymouth, Mass.

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Q: I own a rental home that I could sell for $100,000. Excluding land, I have depreciated $20,000. I know I have to recapture the $20,000 depreciation at 25 percent. Does it matter if I am in the 15 percent tax bracket? I.G., Louisville, Ky.

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Q: We’re interested in setting up an ESOP for a small corporation. Do we need a lawyer or CPA to handle the paperwork? W.S.B.

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Q: I hired a contractor to build a deck on our house for $15,000. We gave him $5,000 up-front for materials, etc. Now he’s skipped out and we can’t find him. Can I deduct the $5,000 deposit as a casualty loss deduction? R.S., Blawenburg, N.J.

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Q: I gave my daughter stock shares that I bought for $10,000. On the day I gave her the shares, they were worth about $12,000. Now, it’s jumped to about $16,000, and I’ve advised her to sell. Is her taxable gain the full $6,000? P.L.A., Santa Barbara, Calif.

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Starting June 27, if you set up a charitable remainder trust (CRT), you’ll need to jump through new IRS hoops.

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