Health insurance deduction on schedule C if also full time employee with w2?
Checkout the worksheet on page 20 of Pub 535.  Also the text starting in the last half of the third column of page 18 onward. https://www.irs.gov/pub/irs-pdf/p535.pdf The fact that you get a W-2 is irrelevant as far as I can see.  Your self-employment business has to meet some criteria (such as being profitable) and the plan needs to be provided through your own business (although if you're sole proprietor filing on Schedule C, it looks like having it in your own name does the trick).  Check the publication for all of the rules. There is this exception that would prevent many people with full-time jobs on W-2 from taking the deduction: Other coverage. You cannot take the deduc­tion for any month you were eligible to partici­pate in any employer (including your spouse's) subsidized health plan at any time during that month, even if you did not actually participate. In addition, if you were eligible for any month or part of a month to participate in any subsidized health plan maintained by the employer of ei­ther your dependent or your child who was un­der age 27 at the end of 2014, do not use amounts paid for coverage for that month to fig­ure the deduction. (Pages 20-21).  Sounds like in your case, though, this doesn't apply. (Although your original question doesn't mention a spouse, which might be relevant to the rule if you have one and he/she works.) The publication should help.  If still in doubt, you'll probably need a CPA or other professional to assess your individual situation. Do you satisfy the necessary criteria listed there? Then why not?... It sounds like you do.
IRS Publication 463 is a great resource to help you understand what you can and can't deduct.  It's not a yes/no question, it depends on the exact company use, other use, and contemporaneous record keeping. Yes, you are the proprietor of the business and your SSN is listed on Schedule C. The information on Schedule C is for your unincorporated business as a contractor; it is a sole proprietorship. You might choose to do this business under your own name e.g. Tim Taylor (getting paid with checks made out to Tim Taylor) or a modified name such as Tim the Tool Man Taylor (this is often referred to as DBA - Doing Business as), under a business name such as Tool Time etc. with business address being your home address or separate premises, and checking accounts to match etc. and all that is what the IRS wants to know about on Schedule C.  Information about the company that paid you is not listed on Schedule C. The idea is that the premiums (or costs) associated with the plan are a business expense, you know that already.  The distinction here is that employees don't pay premiums, they elect to contribute. The company sponsors a plan, the employees then choose to accept less salary in order to participate in the employer's plan.  The idea is that you're foregoing income. Why is the employee not taxed on this cost?  One major reason is that the employee has no say in, and often no idea, what the gross costs are (some find out if they ever receive COBRA election paperwork). There are more benefits than strict healthcare that are Section 125 eligible.  The government has a vested interest in keeping the population healthy, and when the ERISA laws and Section 125 were written it was (and still is) a pretty low friction way to get health insurance out to more people.  At this point, taking away the tax break from the employees would be a huge government take away from most of the population.  Try to get a politician to take something away from taxpayers. Why doesn't the deduction exist in kind to people buying individual coverage?  Ask your legislators.  There are thousands of preferential tax treatment oddities, where some industry will get some sort of benefit or break.  I'm not sure what leads you to think there needs to be some supremely logical reason for this oddity to exit. You can have multiple W2 forms on the same tax return. If you are using software, it will have the ability for you to enter additional W2 forms. If you are doing it by paper, just follow the instructions and combine the numbers at the correct place and attach both.  Similarly you can also have a 1099 with and without a W2. Just remember that with a 1099 you will have to pay the self employment tax ( FICA taxes, both employee and employer) and that no taxes will be withheld. You will want to either adjust the withholding on your main job or file quartely estimated taxes. Travel reimbursement should be the same tax exempt wise. The difference is that with a 1098, you will need to list your business expenses for deduction on the corresponding tax schedule. The value on the 1099 will include travel reimbursement. But then you can deduct your self employment expenses. I believe schedule C is where this occurs. "According to the IRS, it appears there is no issue in a spouse under EE or EE+Child(ren) coverage contributing to an FSA while you contribute to an HSA under an EE Only HDHP account: https://www.irs.gov/pub/irs-drop/rr-05-25.pdf ""In Situation 1, H has HDHP self-only coverage and no other health coverage, is not enrolled in Medicare and may not be claimed as a dependent on another taxpayer’s return. Although W has non-HDHP family coverage, H is not covered under that health plan. H is therefore an eligible individual as defined in section 223(c)(1). The special rules for married individuals under section 223(b)(5) do not apply because W’s nonHDHP family coverage does not cover H. Thus, H remains an eligible individual and H may contribute up to $2,000 to an HSA (lesser of the HDHP deductible for self-only coverage or $2,650) for 2005. H may not make the catch-up contribution under section 223(b)(3) because H is not age 55 in 2005. W has non-HDHP coverage and is therefore not an eligible individual."" Some more information directly from IRS form 969 published for 2015 tax returns: https://www.irs.gov/pub/irs-pdf/p969.pdf Qualifying for an HSA To be an eligible individual and qualify for an HSA, you must meet the following requirements. You must be covered under a high deductible health plan (HDHP), described later, on the first day of the month. You have no other health coverage except what is permitted under Other health coverage, later. You are not enrolled in Medicare. You cannot be claimed as a dependent on someone else's 2015 tax return. Under the last-month rule, you are considered to be an eligible individual for the entire year if you are an eligible individual on the first day of the last month of your tax year (December 1 for most taxpayers). If you meet these requirements, you are an eligible individual even if your spouse has non-HDHP family coverage, provided your spouse's coverage does not cover you." "You will need to see a tax expert. Your edited question includes the line For the short term, we will be ""renting"" it to my wife's grandmother at a deep discount. According to the instructions for schedule E If you rented out a dwelling unit that you also used for personal   purposes during the year, you may not be able to deduct all the   expenses for the rental part. “Dwelling unit” (unit) means a house,   apartment, condominium, or similar property. For each property listed on line 1a, report the number of days in the   year each property was rented at fair rental value and the number of   days of personal use. A day of personal use is any day, or part of a day, that the unit was   used by: I have no idea how this will work for Schedule C." "To claim medical expenses on your taxes they need to exceed 7.5% of your AGI, and then only the amount over 7.5% is deductible.  That's not much.  There is no ""floor"" if you use an FSA as it's all pre-tax. If you're concerned about use or lose, then allot less next year.  It's all what you're comfortable with." It is true that with a job that pays you via payroll check that will result in a W-2 because you are an employee, the threshold that you are worried about before you have to file is in the thousands. Unless of course you make a lot of money from bank interest or you have income tax withheld and you want it refunded to you. Table 2 and table 3 in IRS pub 501, does a great job of telling you when you must.  For you table 3 is most likely to apply because you weren't an employee and you will not be getting a W-2. If any of the five conditions listed below applied to you for 2016, you must file a return. You owe any special taxes, including any of the following. a. Alternative minimum tax. (See Form 6251.)    b. Additional tax on a   qualified plan, including an individual retirement arrangement (IRA),   or other tax­favored account.  (See Pub. 590­A, Contributions to   Individual Retirement Arrangements (IRAs); Pub. 590­B, Distributions   from  Individual Retirement Arrangements (IRAs); and Pub. 969, Health   Savings Accounts and Other Tax­Favored Health  Plans.) But if you are   filing a return only because you owe this tax, you can file Form 5329   by itself.   c. Social security or Medicare tax on tips you didn't   report to your employer (see Pub. 531, Reporting Tip Income) or on    wages you received from an employer who didn't withhold these taxes   (see Form 8919).    d. Write­in taxes, including uncollected social   security, Medicare, or railroad retirement tax on tips you reported to   your  employer or on group­term life insurance and additional taxes on   health savings accounts. (See Pub. 531, Pub. 969,  and the Form 1040   instructions for line 62.)   e. Household employment taxes. But if you   are filing a return only because you owe these taxes, you can file    Schedule H (Form 1040) by itself. f. Recapture taxes. (See the Form   1040 instructions for lines 44, 60b, and 62.) You (or your spouse if filing jointly) received Archer MSA, Medicare Advantage MSA, or health savings account  distributions. You had net earnings from self­employment of at least $400. (See Schedule SE (Form 1040) and its instructions.) You had wages of $108.28 or more from a church or qualified church­controlled organization that is exempt from employer  social   security and Medicare taxes. (See Schedule SE (Form 1040) and its   instructions.) Advance payments of the premium tax credit were made for you, your spouse, or a dependent who enrolled in coverage  through the Health   Insurance Marketplace. You should have received Form(s) 1095­A showing   the amount of the advance  payments, if any. It appears that item 3: You had net earnings from self­employment of at least $400. (See Schedule SE (Form 1040) and its instructions.) would most likely apply. It obviously is not too late to file for 2016, because taxes aren't due for another month. As to previous years that would depend if you made money those years, and how much. If your business is a Sole Proprietorship and meets the criteria, then you would file form Schedule C. In this case you can deduct all eligible business expenses, regardless of how you pay for them (credit/debit/check/cash). The fact that it was paid for using a business credit card isn't relevant as long as it is a true business expense. The general rules apply: Yes - if you sustain a net loss, that will carry over to your personal tax return. Note: even though it isn't necessary to use a business credit card for business expenses, it's still an extremely good idea to do so, for a variety of reasons. "Yes, you can. See the instructions for line 29 of form 1040. Self employed health insurance premiums are an ""above the line"" deduction." Can I work on 1099 from my own company instead of on W2? The reason is   on W2 I can't deduct my commute, Health Insurance and some other   expenses while on 1099 I think I can able do that. Since I am going to   client place to work not at my own office, I am not sure whether I   should able to do that or not. If you have LLC, unless you elected to tax it as a corporation, you need neither 1099 nor W2. For tax purposes the LLC is disregarded. So it is, from tax perspective, a sole proprietorship (or partnership, if multiple members). Being a W2 employee of your own LLC is a bad idea. For all these above expenses, which can I use company's debit/credit   card or I need to use only my personal debit/credit card? It would be better to always use a business account for business purposes. Doesn't matter much for tax per se, but will make your life easier in case of an audit or a legal dispute (limited liability protection may depend on it). If I work on 1099, I guess I need to file some reasonable taxes on   quarterly basis instead of filing at year end. If so, how do I pay my   tax on quarterly basis to IRS? I mean which forms should I file and   how to pay tax? Unless you're a W2 employee, you need to do quarterly estimate payments using form 1040-ES. If you are a W2 employee (even for a different job, and even if it is not you, but your spouse with whom you're filing jointly) - you can adjust your/spouse's withholding using form W4 to cover the additional tax liability. This is, IMHO, a better way than paying estimates. There are numerous questions on this, search the site or ask another one for details. "Even though this isn't really personal finance related I still feel like there are some misconceptions here that could be addressed. I don't know where you got the phrase ""pass-through"" insurance from.  What you're describing is a self-funded plan.  In a self-funded arrangement an employer contracts a third-party-administrator (TPA), usually one of the big health insurance carriers, to use it's provider network, process and adjudicate claims, etc.  In addition to the TPA there will be some sort of stop-loss insurance coverage on each participant.  Stop-loss coverage usually provides a maximum amount of risk on a given member and on the entire population for a given month and/or year and/or lifetime.  The employer's risk is in between the plan deductible and the stop loss coverage (assuming the stop-loss doesn't have a maximum). Almost all of the claim dollars in a given plan will come from very very few people.  These costs typically arise out of very unforeseen diagnoses not chronic issues.  A cancer patient can easily cost $1,000,000 in a year.  Someone's diabetes maintenance medicine or other chronic maintenance will cost no where near what a botched surgery will in a year. If we take a step back there are really four categories of employer insurance. Small group is tightly regulated.  Usually plan premiums are filed with a state authority, there is no negotiating, your group's underwriting performance has zero impact on your premiums.   Employers have no way of obtaining any medical/claim information on employees. Mid-market is a pooled arrangement.  The overall pool has a total increase, and your particular group performs better or worse than the pool which may impact premiums.  Employers get very minor claims data, things like the few highest claims, or number of claims over a certain threshold, but no employee specific information. Large-group is a mostly unpooled arrangement.  Generally your group receives it's own rating based on its individual underwriting performance.  In general the carrier is offloading some risk to a stop-loss carrier and employer's get a fair amount of insight in to claims, though again, not with employee names. Self-funded is obviously self-contained.  The employer sets up a claims checking account.  The TPA has draft authority on the account.  The employee's typically have no idea the plan is self funded, their ID cards will have the carrier logo, and the carrier deals with them just as it would any other member.  Generally when a company is this size it has a separate benefits committee, those few people will have some level of insight in to claims performance and stop-loss activity.  This committee will have nothing to do with the hiring process. There are some new partially self-funded arrangements, which is just a really low-threshold  (and relatively expensive) stop-loss program, that's becoming somewhat popular in the mid-market group size as employers attempt to reduce medical spend.   I think when you start thinking on a micro, single employee level, you really lose sight of the big picture.  Why would an employer hire this guy who has this disease/chronic problem that costs $50,000 per year?  And logically you can get to the conclusion that with a self-funded plan it literally costs the company the money so the company has an incentive not to hire the person.  I understand the logic of the argument, but at the self funded level the plan is typically costing north of half a million dollars each month.  So a mid-level HR hiring manager 1. isn't aware of specific plan claims or costs and is not part of the benefits executive committee, 2. won't be instructed to screen for health deficiencies because it's against the law, 3. a company generally won't test the water here because $50,000 per year is less than 1% of the company's annual medical expenses, 4. $50,000 is well below the cost to litigate a discrimination law-suit.    Really the flaw in your thought process is that $50,000 in annual medical expense is a lot.  A harsh child-birth can run in the $250,000 range, so these companies never hire women?  Or never hire men who could add a spouse who's in child bearing years?  Or never hire women who might have a female spouse who could be in child bearing years?  A leukemia diagnosis will ratchet up $1,000,000 in a year.  Spend a bit of time in intensive care for $25,000 per day and you're fired?  A few thousand bucks on diabetes meds isn't anything relative to the annual cost of your average self-funded plan. The second flaw is that the hiring managers get insight in to specific claims.  They don't. Third, you don't hand over medical records on your resume anyway. I typed this out in one single draft and have no intention of editing anything.  I just wanted paint a broad picture, I'm sure things can be nit-picked or focused on." It would be unusual but it is possible that the expenses could be very high compared to your income. The IRS in pub 529 explains the deduction. You can deduct only unreimbursed employee expenses that are: Paid or incurred during your tax year, For carrying on your trade or business of being an employee, and Ordinary and necessary. An expense is ordinary if it is common and accepted in your trade,   business, or profession. An expense is necessary if it is appropriate   and helpful to your business. An expense doesn't have to be required   to be considered necessary. The next part lists examples. I have cut the list down to highlight ones that could be large. You may be able to deduct the following items as unreimbursed employee   expenses. Damages paid to a former employer for breach of an employment contract. Job search expenses in your present occupation. Legal fees related to your job. Licenses and regulatory fees. Malpractice insurance premiums. Research expenses of a college professor. Rural mail carriers' vehicle expenses. Tools and supplies used in your work. Work clothes and uniforms if required and not suitable for everyday use. Work-related education. If the term of employment was only part of the year, one or more of the these could dwarf your income for the year. Before deducting something that large be sure you can document it. I believe the IRS computers would flag the return and I wouldn't be surprised if they ask for additional proof. For a 401(k), only contributions that you make for the current tax year through payroll deduction are tax-deductible.  Those contributions are subtracted off of your income for your W-2 Box 1 income amount.  If you make a manual contribution to your 401(k) outside of that, it is not tax deductible, and there is nowhere on your Form 1040 to deduct it. Your commuter benefits are also paid for out of payroll deduction and deducted on your W-2, so this is not an option, either. You could contribute to a traditional IRA for last year up to your tax return deadline, and deduct the amount on Form 1040 Line 32.  However, because you have access to a retirement plan at work, your IRA contribution is only tax deductible if your income is below certain limits. "Model 3 passed all regulatory requirements for production two weeks ahead of schedule. Expecting to complete SN1 [Serial Number 1] on Friday, Tesla (NASDAQ:TSLA) CEO Elon Musk tweeted on Sunday.  ""Handover party for first 30 customer Model 3's on the 28th! Production grows exponentially, so Aug should be 100 cars and Sept above 1500... Looks like we can reach 20,000 Model 3 cars per month in Dec.""  The car, which already has over 400,000 pre-orders, is Tesla's cheapest vehicle to date - starting at $35,000.  TSLA +3% premarket"