To know if the S corporation is the best choice of entity for your business, first you need to consider three advantages and nine disadvantages. Next, you need to take the S corporation advantages and disadvantages that apply to you and get a bottom-line number comparison with your second choice for an operating entity. In this way, you can make a logical choice, knowing that your best choice will stay with you for a number of years and let you pocket more after-tax cash while you sleep better at night.

When you and/or your spouse own more than one business, you must look at all businesses as one business when applying the Section 105 medical reimbursement plan discrimination rules. If you are blocked by the discrimination rules, consider discriminating in health insurance coverage to your benefit.

The appeals court remanded the Shellito case back to the Tax Court along with its road map for establishing the Section 105 plan. In the right circumstances, the 105 medical plan creates tax deductions where none existed before, and its tax-free fringe benefits can operate as the sole remuneration to the employee-spouse.

With proper planning, you can use two exceptions to add a Section 105 plan, FSA, or HRA to your HSA.

If you are married, operate your business as a proprietorship, and have only your spouse as an employee, you likely want a Section 105 medical reimbursement plan that can turn most, if not all, of your medical expenses into business deductions on your Schedule C. Before health care reform, you did not need to give your employee-spouse a W-2 for Section 105 medical plan reimbursements. Now, thanks to the IRS, the Section 105 medical reimbursement W-2 requirement for small businesses does not apply before the 2014 W-2 reporting season—and may not apply afterward.

The IRS changed its 1040 instructions to allow the proprietorship and single-member LLC a self-employed health insurance deduction for Medicare Part B. The impact on the S corporation owner is not as favorable.

The new under-age-27 health insurance coverage grants windfalls, pitfalls, and planning opportunities.

Tax law creates trouble for selected fringe benefits that the S corporation gives to a more than 2 percent shareholder. The loss of benefits and accompanying complications are factors to consider in the selection of the S corporation as your choice of business entity.

New guidance from the IRS on the new health care law says the owner of a business (proprietorship, corporation, LLC, etc.) may not claim the 35 percent tax credit on the health insurance premiums paid to cover his or her spouse.

The new health care law changes the requirements for deducting vitamins in your Section 105 medical reimbursement plan.

This issue contains 21 last-minute tax tips that you can use for 2010. We broke the tips into two articles: one for vehicles and one not related to vehicles. This article contains 12 last-minute tax tips that are not related to vehicles.

The IRS just clarified the Section 105 medical reimbursement plan rules for deducting over-the-counter drugs in 2011. Read this article to get updated. Then, download a sample Section 105 medical reimbursement plan document that your business can use to comply with both 2010 and 2011 requirements.

The new health care law grants a nice tax credit to business owners who cover their employees. How about the owners themselves? Lawmakers did them no favors, but one group of proprietors might catch a break.

For business owners who have children ages 22, 23, 24, 25, and 26, the new health care bill contains a healthy break, and perhaps even better than that. Amend Section 105 plans now for this new provision. Download your sample plan from this article.

The S corporation owner is an employee of his or her corporation. Thus, his or her personal payment of health insurance does not qualify for deduction on page 1 of the Form 1040. To get this page 1 deduction, the IRS says that the health insurance must be paid by the corporation and come to the owner on a W-2.

Use this Section 105 medical reimbursement plan template to make sure you provide maximum medical benefits to you and your family while legally discriminating under both tax law and ERISA rules.

As the end of the year arrives, you still have time to pocket some tax money. The 20 strategies in this article have a wide range, from getting married to selling your old vehicle. Spend a few minutes and pick up some last minute tips.

When a couple owns an LLC, they can obtain the benefits of a section 105 medical plan by filing as a single member LLC.

Which is better: paying medical insurance out of your pocket, or forming a C corporation to deduct the insurance costs? The extra tax on the corporation might outweigh the insurance deduction. Or, it might not.

Under tax law, Medicare B can be deducted as health insurance. We have proof. Also, we show you how to get the Medicare premium to qualify as an employer plan, and how to relate it to the earned income of your business.

Section 105 uses a definition of medical that is broader than that for an itemized deduction. This broadening allows you to deduct supplements and over the counter drugs to treat injuries and illness.

The Section 105 Medical Plan is filled with important details that you can’t afford to miss. Learn from the Knowles’ problems in court to see what you can do better.

This is our grand summary of the inner workings of Section 105 medical reimbursement plan. Use it wisely!

We answer one taxpayer’s question about S corporation medical benefits. We also help him decide which is better for his wife’s business: S corporation, C corporation, or single-member LLC.

You might be able to deduct Medicare payments as medical insurance premiums, but it depends which type of Medicare you have.

It is so important to know the law. We give support to a good CPA against an unreasonable IRS auditor about part-time employees’ medical benefits under Section 105.

CPAs are not always right! One couple tries to get Section 105 benefits, and is incorrectly refuted by their accountant. We give evidence to support our position, and advice on how to get Section 105 benefits.

The Section 105 medical reimbursement plan is a terrific tax-planning tool for the husband-and-wife business. But, as with any tax-reduction tactic, doing it right is critical.

In an ISP, the IRS asserted that the Section 105 medical reimbursement plan may not reimburse the employee-spouse for the cost of health insurance purchased in the employee-owner’s name. This court case held that this IRS position is wrong and that the owner may deduct the cost of medical insurance purchased in his name when that insurance is covered by the Section 105 medical reimbursement plan.

Answering “yes” to the 11 puts you on the road to audit-proof status for your Section 105 medical reimbursement plan.

Meal replacements, diet foods, and dietary supplements are substitutes for the food individuals normally consume, making them nondeductible personal expenses.

An inversion table lets someone hang upside-down by the ankles to alleviate back pain. According to tax law, it can be deducted as a medical expense.

Deducting a piece of furniture, like a back chair, is tricky. You can do it, but you have to be very precise. For example, we recommend supporting your position by getting a prescription, and building proof that this chair would not be used generally as an article of furniture

Darwin Albers employed his wife and claimed an $8,216 section 105 medical reimbursement plan deduction. He lost every penny of his claimed 105 medical reimbursements because of a few easily avoided errors.

If your spouse is working for your company, you need proof that s/he is a legitimate employee. It is not hard, but you need to have good, solid proof to ensure that your deductions and medical reimbursements will be honored by the IRS.

Learn about one couple’s problems with Section 105 medical reimbursement. You must document all payments. The reimbursement of the employee-spouse for every medical bill is easily done and a audit-proofing tactic. Make this an absolute requirement.

If your spouse is working for your company, you need proof that s/he is a legitimate employee. It is not hard, but you need to have good, solid proof to ensure that your deductions and medical reimbursements will be honored by the IRS.

Learn about one couple’s problems with Section 105 medical reimbursement. You must document all payments. The reimbursement of the employee-spouse for every medical bill is easily done and a audit-proofing tactic. Make this an absolute requirement.

For employees under the Section 105 Medical Plan, the law authorizes a medical deduction for transportation to receive medical care. You may reimburse any medical expense that you could otherwise deduct on your Form 1040.

The tax law allows you to deduct the cost of laser eye surgery, as long as it produces a business benefit. There are specific details that apply, though, so read carefully.

You get no business benefit from the section 105 plan at the S corporation level. However, you do get a big personal benefit when you steer the medical insurance through the S corporation to give yourself the medical insurance as a guaranteed payment.

Vitamin use falls into two different categories depending if you reimburse them under Section 105 Medical Plan or file them in your tax returns under your 1040.

Here’s an example of a perfect plan for using the Section 105 Medical Reimbursement Plan for an employee-spouse in a single proprietorship.

It is possible to save big on medical insurance if you use the Section 105 Medical Reimbursement Plan. If you navigate the tax law correctly, you might be able to save $4,000, like one taxpayer. Knowledge is power.

If you hire your spouse, you can save a lot of money in taxes by not paying him/her a wage. Instead, cover him/her and your family with medical benefits under Section 105.

When the husband and wife work together in the business, but report that business on one Schedule C, they create a tax problem for themselves. Is this a partnership or joint venture where both husband and wife have earned income subject to self-employment taxes? You can avoid this problem by hiring the spouse not reporting on a Schedule C. You then can avoid payroll taxes on the wages to the employee-spouse by making the compensation non-W-2 income.

When designing the medical plan, you need to consider all your and your spouse’s proprietorships, LLCs, and corporations as one business. If employees exist in one of these businesses, you have employees in all businesses. Plan your discrimination or nondiscrimination accordingly.

The more than 2 percent owner of an S corporation may not benefit from a fringe benefit like corporate paid health insurance. Further, this owner-employee is not “self employed” for purposes of deducting self-employed health insurance on page 1 of IRS Form 1040. This leaves the more than 2 percent owner with only one IRS approved method for gaining the maximum deduction from health insurance.

In Chief Counsel Advice, the IRS clarified its position that a sole proprietor may deduct the cost of health insurance on his or her Form 1040 regardless of whether the insurance is purchased in the individual’s or the proprietorship’s name.

The W-2 reporting requirements exempt the Section 105 medical plan reimbursements from entries on the W-2.

This court case provides a great roadmap to the Section 105 medical reimbursement plan. The taxpayer hired her husband as a part-time employee. The husband had another job as a full-time employee where he elected a payroll deduction for a medical plan that covered himself and his family. In her proprietorship, the wife put a Section 105 medical plan in place that covered the employee-husband. He elected family coverage, and presto, the monies he paid to his full-time employer for medical coverage became a Section 105 medical reimbursement, deductible by the wife’s proprietorship.

In 1935, the self-employment tax topped out at $60. In 2006, the first part of the self-employment tax tops out at $14,413, but the 2.9 percent Medicare part continues after that without limits. Good tax planning for the self-employment tax is like an annuity. It gives you monetary returns—year after year—every year you are in business. So, plan now and consider everything from choice of entity to hiring your children.