Comparing/reviewing personal health insurance plans for the self-employed
I was in your situation a few years ago and I discovered something that worked perfectly for me - a local health insurance broker. I met with her, discussed my needs, reviewed the options with her, then acted. She received a commission from the insurer, so it cost me nothing. I would certainly follow a similar approach again. Here's an old-ish article from the NYT that discusses this. Health insurance is tough, as you know, because the offerings vary dramatically by State, and there is the added complication of the Affordable Care Act, which depending on where and who you are has had either a good or bad impact on the available options. If you are a sole proprietor or other business person, I'd advise talking to someone at a local chamber of commerce. Also, professional organizations like the IEEE or ACM (for IT professionals) often offer catastrophic medical or other health plans. Some employer plans give you the option to continue coverage at a higher cost when COBRA lapses as well. If you can't afford a comprehensive plan, make sure to get something to protect you against pre-existing conditions or hospitalization.
The HSA money is yours to keep. You can't add new money into the account and get a tax deduction for the new money, but you can spend the old money on medical expenses. First log into the website for the HSA and see if you have money left. This can be important because if there is still money left they might be charging you a monthly fee. You should have gotten a letter from the old company or the administrator when you left the High deductible insurance plan. This would have told you your options regarding the spending or transferring of old funds. HSA related numbers would have appeared on your W2, and you should have a 1099-SA from the administrator. It is likely that there is a copy of the 1099 on the administrators website. The numbers you enter on the tax forms depends on how much you contributed from your paycheck, how much your company contributed, and how much you sent (if any) from other sources besides payroll deduction. You will also have to know how much money was withdrawn from the HSA and how much was used for medical purposes. The last month rule is for those people who start in the middle of the year. If you start partway through the year you are allowed to make the maximum contribution if you still have it at the end of the year, and you expect to keep it.  The Last Month Rule The Last Month Rule states that if you are covered by an HSA eligible   health plan on the first day of the last month of a given year, you   are considered an eligible individual for the entire year. In turn,   you can then contribute to the HSA for that full year. If you are covered by an HDHP on Dec 1st of a given year, you may contribute the maximum for that year. For example, you could begin coverage and open up my HSA in November   of a given year. Come December 1st, you are covered and per the Last   Month Rule, considered an eligible employee for that full year. That   allows you to contribute up to that year’s contribution limit, even   waiting a few months to make a prior year contribution if you like.   Back up the truck and load up the HSA! However, there is a catch.  The Testing Period The Testing Period states if you use the Last Month Rule, you must   remain an eligible individual (covered by HDHP) for the following 12   months. If you fail to remain an eligible individual (change insurance   plans, lose insurance plan, receive other health coverage) any “extra”   contributions you made as a result of the Last Month Rule will be   taxed and penalized. If you contribute per the Last Month Rule and end your HDHP insurance within 1 year, you will have to pay tax on any excess   contributions you were allowed to make and pay a 10% penalty. In this case, “excess” contributions are determined by the   contribution limit / 12 months, compared to your time eligible. For 2014/15 it looks something like this:  To make it a bit clearer, let's also plot the difference in net income for self-employment and a single person company compared to employment:  Self-employment is slightly worse between £5885 and about £10,500 because Class 2 NI kicks in before the employed person starts paying any tax. After that, self-employment is better because you pay 9% Class 4 NI rather than 12% Class 1 NI. Once higher rate tax kicks in, the saving stops growing. The single-person company is most tax-efficient at all points, ignoring any accountancy costs it incurs. Strange things happen between £100k and about £135k because the withdrawal of the personal allowance kicks in at a different point when receiving dividends. We can also plot the percentage of income paid as tax for each case:  The strange kink for self-employment below £10k is caused by Class 2 NI again. Employment and self-employment both gradually tend towards paying 47%, reaching 46.5% for £2m gross income. The company tends towards 44.44%, reaching 43.6% for £2m gross income. The answer seems to depend on where you live.  Perhaps you already found this, but the summary from the IRS is: The insurance laws in some states do not allow a corporation to purchase group health insurance when the corporation only has one employee. Therefore, if the shareholder was the sole corporate employee, the shareholder had to purchase his health insurance in his own name. The IRS issued Notice 2008-1, which ruled that under certain situations the shareholder would be allowed an above-the-line deduction even if the health insurance policy was purchased in the name of the shareholder. Notice 2008-1 provided four examples, including three examples in which the shareholder purchased the health insurance and one in which the S corporation purchased the health insurance. Notice 2008-1 states that if the shareholder purchased the health insurance in his own name and paid for it with his own funds, the shareholder would not be allowed an above-the-line deduction. On the other hand, if the shareholder purchased the health insurance in his own name but the S corporation either directly paid for the health insurance or reimbursed the shareholder for the health insurance and also included the premium payment in the shareholder’s W-2, the shareholder would be allowed an above-the-line deduction. The bottom line is that in order for a shareholder to claim an above-the-line deduction, the health insurance premiums must ultimately be paid by the S corporation and must be reported as taxable compensation in the shareholder’s W-2. https://www.irs.gov/Businesses/Small-Businesses-&-Self-Employed/S-Corporation-Compensation-and-Medical-Insurance-Issues I understand this to mean that you can only get the deduction in your case (having purchased it in your own name) if your state does not allow your S-Corp to purchase a group health plan because you only have one employee. (I don't know specifically if Illinois fits that description or not.)  In addition, there are rules about reporting health insurance premiums for taxes for S-Corp share members that you should also check.  Personally, I think that it's complicated enough that advice from a CPA or other tax advisor specific to your situation would be worth the cost. HSA rules are different in some regards than deductions allowable under Pub 502 which deals with medical expenses deductible in Schedule A of your tax return. Pub 969 governs HSA's and similar reimbursement plans, and the guidelines are as follows: Insurance premiums. You can’t treat insurance premiums as qualified medical expenses unless the premiums are for: -Long-term care insurance. -Health care continuation coverage (such as coverage under COBRA). -Health care coverage while receiving unemployment compensation under federal or state law. -Medicare and other health care coverage if you were 65 or older (other than premiums for a Medicare supplemental policy, such as Medigap). Since your wife is still being treated like an employee for health benefits, and you are not on COBRA, thus not eligible for a deduction. You may qualify under the unemployment provision depending on the cause of her disability. There are a lot of moving parts, individual premiums and annual increases have little to do with employer premiums and annual increases and vice versa.  Most people think of XYZ insurer as a single company with a single pool of insured folks.  This common knowledge isn't accurate.  Insurers pool their business segments separately.  This means that Individual, small business, mid-size business, and large business are all different operating segments from the viewpoint of the insurer.    It's possible to argue that because so many people are covered by employer plans that individual plans have a hard time accumulating the required critical mass of subscribers to keep increases reasonable.   Age banded rating: Individual coverage and small group coverage is age rated, meaning every year you get older.  In addition to your age increase, the premium table for your plan also receives an increase.  Employers with 100+ eligible employees are composite rated (in general), meaning every employee costs the same amount.  The 18 year old employee costs $500 per month, the 64 year old costs $500 per month.  Generally, the contributions an employee pays to participate in the plan are also common among all ages.  This means that on a micro level increases can be more incremental because the employer is abstracting the gross premium.  Composite rating generally benefits older folks while age rating generally benefits younger folks. Employer Morale Incentive: Generally the cost to an employee covered by an employer plan isn't directly correlated to the gross premium, and increases to the contribution(s) aren't necessarily correlated to the increases the employer receives.  Employers are incentivised by employee morale.  It's pretty common for employers to shoulder a disproportionate amount of an increase to keep everyone happy.  Employers may offset the increase by shopping some ancillary benefit like group life insurance, or bundling the dental program with the medical carrier.  Remember, employees don't pay premiums they pay contributions and some employers are more generous than others.  Employers are also better at budgeting for planned increases than individuals are. Regulators: In many of the states that are making the news because of their healthcare premium increases there simply isn't a regulator scrutinizing increases.  California requires all individual and small group premiums to be filed with the state and increases must be justified with some sort of math and approved by a regulator.  Without this kind of oversight insurers have only the risk of subscriber flight to adjust plan provisions and press harder during provider contract negotiations. Expiring Transitional Reinsurance Fee and Funds: One of the fees introduced by healthcare reform paid by insurers and self-insured employers established a pot of money that individual plans could tap to cope with the new costs of the previously uninsurable folks.  This fee and corresponding pot of money is set to expire and can no longer be taken in to account by underwriters. Increased Treatment Availability: It's important that as new facilities go online, insurer costs will increase.  If a little town gets a new cancer clinic, that pool will see more cancer treatment costs simply as a result of increased treatment availability.  Consider that medical care inflation is running at about 4.9% annually as of the most recent CPI table, the rest of the increases will result from the performance of that specific risk pool.  If that risk pool had a lot of cancer diagnoses, you're looking at a big increase.  If that risk pool was under priced the prior year you will see an above average increase, etc. My dad runs an AV labor company (trade show setups etc) and his insurance company called him as they were finalizing his workers comp. They asked when he was submitting all of his employees drug screenings. My dad laughed at them and said he would not be submitting any. They told him his premium would be higher to which my dad replied that if he drug tested, he would have 4 people working for him and thus wouldn't even have a business - just send the bill. I would prefer to see you register in your home state, and then focus on making money, rather than spending time looking to game the system to save a few bucks.  People worry way too much about these trivial fees when they should be focused on making their business successful.  Get registered, get insurance, and then pour it on and start making money. Make $650 your target for a week's income - you can do it!  Next year's goal should be spending $50 a month on a payroll service because you're SO BUSY you can't take the extra time to pay your own social security taxes. "Am I on crack, or do the perceived tax savings via S-Corp   distributions really not matter at a certain level of business income? You're not on crack. Generally, if all the income is generated by your own personal services - this is the outcome. The benefit of S-Corp is when you have employees who generate your income, and you distribute to yourself profits that come out of other's personal services. In this case your distributions are exempt from FICA since it is not in fact a self-employment income. You'd still have to pay yourself a reasonable salary for your position (as a manager/officer), but it wouldn't have to cover all of the available profits. So if the IRS takes a position against you it would be that your salary should be to include the whole profits, since it is the compensation to you for the personal services that produced the income to the corporation (you). In many cases they might agree that a salary at the SS maximum limit would be reasonable - but that's only a speculation of mine. In that case you might gain some portion of the medicare tax (with the recent law changes at the levels you're talking about you'll pay some medicare anyway). There are a lot of accountants who take more aggressive position saying that not all of the distributions are liable for SE taxes, even if you're the sole employee of the corporation. These cases often end up in the Tax Court, and whatever the outcome, your legal fees become higher than the FICA savings. What is probably missing in your picture is the SS limit of (currently $112K) above which you don't pay social security tax, so whether you get it as a salary or as a distribution - that limit is the same. That is why you don't see a significant difference. I know there are a lot of accountants who'd disagree, but I would argue that for a sole employee of your company, S-Corp doesn't provide significant benefits over the disregarded LLC taxation, but has some additional overhead that adds to your expenses. Here's a link to a lawyer's blog where he suggests (and says many accountants follow) 60/40 division between salary and distributions. I.e.: his take, similarly to mine, is that most of the earnings have to be treated as salary. In your case, when the total is about 300K - you indeed will not get any FICA savings with such a division other than some of the medicare.  Unusually low wages when compared to distributions can draw unwanted   IRS scrutiny and an audit. An unfavorable audit will likely result in   some portion of the distributions being reclassified as earned income   for federal income tax purposes, which results in a deficiency   assessment (i.e., a tax bill), interest on those unpaid taxes, and IRS   penalties. The article also talks about the Watson case (one of the Tax Court cases I referred to), which can be used as the guidelines for determining the ""reasonable"" compensation. Talk to your tax adviser. I'm neither a tax adviser nor a tax professional. For a tax advice contact a CPA/EA licensed in your state. This is not a tax advice, just my personal opinion."