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.
"I agree that you should have received both a 1099 and a W2 from your employer. They may be reluctant to do that because some people believe that could trigger an IRS audit. The reason is that independent contractor vs employee is supposed to be defined by your job function, not by your choice. If you were a contractor and then switched to be an employee without changing your job description, then the IRS could claim that you should have always been an employee the entire time, and so should every one of the other contractors that work for that company with a similar job function. It's a hornet's nest that the employer may not want to poke. But that's not your problem; what should you do about it? When you say ""he added my Federal and FICA W/H together"", do you mean that total appears in box 4 of your 1099? If so, it sounds like the employer is expecting you to re-pay the employer portion of FICA. Can you ask them if they actually paid it? If they did, then I don't see them having a choice but to issue a W2, since the IRS would be expecting one. If they didn't pay your FICA, then the amount this will cost you is 7.65% of what would have been your W2 wages. IMHO it would be reasonable for you to request that they send you a check for that extra amount. Note: even though that amount will be less than $600 and you won't receive a 1099 in 2017 for it, legally you'll still have to pay tax on that amount so I think a good estimate would be to call it 10% instead. Depending on your personality and your relationship with the employer, if they choose not to ""make you whole"", you could threaten to fill out form SS-8. Additional Info: (Thank you Bobson for bringing this up.) The situation you find yourself in is similar to the concept of ""Contract-to-Hire"". You start off as a contractor, and later convert to an employee. In order to avoid issuing a 1099 and W2 to the same person in a single tax year, companies typically utilize one of the following strategies: Your particular situation is closest to situation 2, but the reverse. Instead of retroactively calling you a W2 employee the entire time, your employer is cheating and attempting to classify you as a 1099 contractor the entire time. This is frowned upon by the IRS, as well as the employee since as you discovered it costs you more money in the form of employer FICA. From your description it sounds like your employer was trying to do you a favor and didn't quite follow through with it. What they should have done was never switch you to W2 in the first place (if you really should have been a contractor), or they should have done the conversion properly without stringing you along." "I have done several days of additional research on this and found out that it appears I can deduct the cost of the books against a single year's royalty income by claiming a Section 179 deduction. The steps are as follows: (1) Write the maximum amount of property you can claim under section 179 on line 1 of Form 4562. (2) Add up the total cost of section 179 property you began using during the tax year, including books, and record the amount on line 2. (3) Write the limit of your deductions on line 3. (4) Subtract the amount on line 2 from the amount on line 3 and record it on line 4. If line 3 is larger than line 2, simply write ""0"" on line 4, then subtract the amount on line 4 from the amount on line 1 and record on line 5. Step 5 (5) Describe the property and books on line 6 and record the cost of each in section b. Write the amount of the expense you are claiming for each item in section c of line 6. You can claim the entire cost of the books. (6) Add the amount in line 6 c to any amounts on line 7 and write the total on line 8. Write either the amount on line 8 or the amount on 5 on line 9, depending on which is smaller. (7) Write the amount of your Schedule C income on line 11, unless it is greater than $500,000. On line 12, write the amount of your deduction, which is the total of line 9 plus any carry-over you may have had from the previous year. (8) Record the amount of your deduction for section 179 books and property on line 13 of your Schedule C, not line 22. Include form 4562 when you hand in your tax return. source: ""How to Deduct Books for Self-Employed"" by Emily Weller" You need to report the interest expense, assuming the loans were for your business: You need to report interest expense (only interest, principle is not an expense just as the loan proceeds are not income). The interest expense goes to the appropriate line on your Schedule C or E (depending on whether you used the loan for the online business or the rental). People whom you borrowed from must also report the interest as income to them on their Schedule B. You cannot deduct the interest expense if they don't report it as interest income. If you didn't take the loans for your business then the interest is not deductible. You don't need to report anything. People who lent you money still have to report the interest you paid to them as income on Schedule B. If you paid no interest (free loan) or below/above market interest to a related party (family member), then the imputed interest is considered income to them and gift to you. They need to report it on their Schedule B, and depending on amounts - on a gift tax return. For $1K to $10K loans there probably will be no need in gift tax returns, the exemption is for $14K per year per person. If the imputed interest rules may apply to you, better talk to a licensed tax adviser on how to proceed. "In my experience, there is one aspect of HSA's that people often overlook.  In an HSA you will not have ""nice"" copays nor will co-insurance kick in until you have met the deductible (always double-check the summary of benefits, but this is a defining characteristic of HSA plans).   This first-dollar responsibility is something shared by all HSAs (US gov't calls them Qualified High-deductible Health Plans).  In exchange for the nice tax-benefits, the government wants HSA subscribers to pay the full amount for provided services until they meet their deductible (theory being that this will reduce the demand for unnecessary medical services).     Check the summary of benefits for more specifics, but you should not be surprised to learn that this applies to Prescription Drugs as well as any doctor or hospital services (i.e. you would pay the insurer's negotiated price for prescriptions until you've paid $1500 out of pocket).  And that is one area that surprises many first-time HSA subscribers." "Chris, Joe's table helps.  but think this way:  there are two ways you can pay the taxes for your side-gig:  either you can send a check quarterly to the Feds, OR, you can overwithhold at your real job to cover taxes at your sidegig.  I'd do this in ""arrears"" -- after you get your first paycheck from sidegig, then adjust your real job's withholding. Except (and Joe neglected this), you're still responsible for Social Security / Medicare Tax from your sidegig.  I suspect your income at real-job is high enough that you stop paying Social Security Tax, so at least at this time of year you won't be subject to 15.4% Social Security Tax.  However, that's NOT true for the 2.9% Medicare Tax.  Remember that because you're an independent contractor being payed without withholding, YOU are responsible not only for the Medicare (and Social Security) taxes you'd be responsible for if a regular employee, but you're also responsible for what your employer's share as well." The general rule is: Generally, in order to claim a business deduction for your home, you must use part of your home exclusively and regularly: Exclusively seems to be the toughest standard and I do not know exactly how strict the IRS's interpretation is. Working in your living room where you regularly watch TV and have people over on the weekends would seem to fail that test. A separate room with your computer in it would pass it. If it was your only computer and you regularly played online games with it, that would seem to be a grey area.  The IRA booklet covering this area is here http://www.irs.gov/pub/irs-pdf/p587.pdf I know people that have rented rooms in other places or made use of rental offices for this purpose. "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." "Short answer: Yes. For Federal income tax purposes, you are taxed on your total income, adding up positives and negatives. If business A made, say, $100,000 while business B lost $20,000, then your total income is $80,000, and that's what you'll be taxed on. As @littleadv says, of course any business losses you claim must qualify as business losses under IRS rules. And yes, there are special rules about losses that the IRS considers ""passive"". If you have wage income in addition to business income, business losses don't offset wage income for social security and medicare tax purposes. You can't get a refund of the social security tax deducted from your paycheck. I don't know if this is relevant to you, but: If you have businesses in different states, each is taxed by that state. For example I have two tiny side businesses, one in Michigan and one in Ohio. Last year the Michigan business made money while the Ohio business lost money. So my federal income was Michigan minus Ohio. My Ohio income was negative so I owed no Ohio income tax. But I couldn't subtract my Ohio losses from my Michigan income for Michigan income tax purposes. Thus, having, say, $10,000 income in Michigan and $10,000 in Ohio would result in lower taxes than $30,000 income in Michigan and a $10,000 loss in Ohio, even though the total income in both cases is the same. And this would be true even if the tax rates in both states were identical."