If I take a loss when I sell my car, can I claim a capital loss deduction on my income tax return?
"While you'd need to pay tax if you realized a capital gain on the sale of your car, you generally can't deduct any loss arising from the sale of ""personal use property"". Cars are personal use property. Refer to Canada Revenue Agency – Personal-use property losses.  Quote: [...] if you have a capital loss, you usually cannot deduct that   loss when you calculate your income for the year. In addition, you   cannot use the loss to decrease capital gains on other personal-use   property. This is because if a property depreciates through personal   use, the resulting loss on its disposition is a personal expense. There are some exceptions. Read up at the source links."
As a general rule, you must choose between a mileage deduction or an actual expenses deduction.  The idea is that the mileage deduction is supposed to cover all costs of using the car.  Exceptions include parking fees and tolls, which can be deducted separately under either method.  You explicitly cannot deduct insurance costs if you claim a mileage deduction.   Separately, you probably won't be able to deduct the deductible for your car as a casualty loss.  You first subtract $100 from the deductible and then divide it by your Adjusted Gross Income (AGI) from your tax return.  If your deductible is over 10% of your AGI, you can deduct it.   Note that even with a $1500 deductible, you won't be able to deduct anything if you made more than $14,000 for the year.  For most people, the insurance deductible just isn't large enough relative to income to be tax deductible.   Source "Document how you came to have the stuff in the first place. First to defend against potential government inquiry; and second to establish that you held the asset more than one year, so you qualify for long-term capital gains rate.  I wouldn't sell it privately all at once, if you can avoid it.   If you can prove you held it more than a year,  you should pay the long-term capital gains tax rate, which is fairly low.  You'll keep most of it.  A huge windfall often goes very badly. People don't change their financial habits, burn through their winnings shockingly fast, overspend it, and wind up deep in debt.  At the end of the crazy train, their lives end up worse.   That wasn't your question, but you'll do better if you're on guard for that, with good planning and a desire to invest it in things which give you deferred income in the future. That's the cooler thing, when your investments mean you don't have to go to work! I don't mean donate ALL of it to charity. But feel free.  If you hold a security more than one year, and donate it to charity, you get a tax deduction for the appreciated value (even though the security didn't actually cost you that). (link) Do not convert the BTC to cash then donate the cash. Donate it as BTC.  Your tax deduction works against your highest tax bracket.  If you are paying in a 28% tax bracket (your next $100 of income has $28 tax), then for every $100 of charitable donation, you get $28 back on Federal. It does the same to state tax, and you also avoid the 10-15% capital gains tax because you didn't sell the securities.  Do your 1040 both ways and note the difference.***** Your charitable deduction of appreciated securities is capped at 30% of AGI.  Any excess will carryover and becomes a tax deduction for the next year, and it can carryover for several years. **  Use a donor-advised fund. If you have are donating more than $5000, you don't need to search for a charity that will take Bitcoin, and you also don't need to pick a charity now.  Instead, open a special type of giving account called a Donor-Advised Fund.  The DAF, itself, is a charity. It specializes in accepting complex donations and liquidating them into cash.  The cash credits to your giving account.  You take the tax deduction in the year you give to the DAF.  Then, when you want to give to a charity, you tell the DAF to donate on your behalf***.   You can tell them to give on your behalf anonymously, or merely conceal your address so you don't get the endless charity junk mail.   The DAF lets you hold the money in index funds, so your ""charity nest egg"" can grow with the market.  Mine has more than doubled thanks to the market.  This money is no longer yours at this point; you can't give it back to yourself, only to licensed charities. The Fidelity Donor Advised Fund makes a big thing of taking Bitcoin, and I really like them. **** I love my DAF, and it has been a charitable-giving workhorse.  It turns you into a philanthropist, and that changes you life in ways I cannot describe. Certainly makes me more level-headed about money.   Lottery winner syndrome is just not a risk for me (partly because I'm now on the board of charities, and oversee an endowment.)  Donating generally will reduce suspicion (criminals don't do that), but donating to a DAF even moreso.  Since the DAF would have to return ill-gotten gains, they're involved.  Their lawyers will back you up.  The prosecutor is up against a billion dollar corporation instead of just you.  With Fidelity particularly, Bitcoin is a crusade for them, and their lawyers know how to defend Bitcoin.  A Fidelity DAF is a good play for that reason alone IMO.  ** The gory details: Presumably you are donating to regular charities or a Donor Advised Fund, and these are ""50% limit organizations"". Since it's capital gains, you have a 30% limit. If your donation is more than 30% of AGI, or if you have carryover from last year, you use Worksheet 2 in Publication 526. You plug your donations into line 4, then the worksheet grinds through all the math and shows what part you deduct this year and what part you carryover to the next year.  *** I specifically asked managers at two DAFs whether they were OK with someone donating a complex asset to the DAF, and immediately giving the entire cash amount to a charity.  The DAF doesn't get any fees if you do that.  They said not only are they OK with it, most of their donors do exactly that and most DAF accounts are empty.  They make it on the 0.6% a year custodial fee on the other accounts, and charitable giving to them.    Mind you, you can only donate to 501C3 type charities, what IRS calls ""50% limit organizations"".  This actually protects you from donating to organizations who lie about their status.  **** I'm not with Fidelity, but I am a satisfied DAF customer.  The DAF funds its overhead by deducting 0.6% per year from your giving account. If you invest the funds in a mutual fund within the DAF, that investment pays the 0.08% to 1.5% expense ratio of the fund.   I can live with that.  ***** I just Excel'd the value of donating $100 of appreciated security instead of taking it as capital gains income.  28% Fed tax, 15% Fed cap gains, 8% state tax on both.  Take the $100 as income, pay $23 in cap gains tax.  Donate $100 in securities, the $23 tax goes away since you didn't sell it. Really.  The $100 charitable deduction offsets $100 in income, also saving you $36 in regular income tax.  Net tax savings $59.  However you lost the $100!  So you are net $41 poorer.  It costs you $41 to donate $100 to charity.  This gets better in higher brackets." Yes, if you can split your income up over multiple years it will be to your advantage over earning it all in one year.  The reasons are as you mentioned, you get to apply multiple deductions/credits/exemptions to the same income. Rather than just 1 standard deduction, you get to deduct 2 standard deductions, you can double the max saved in an IRA, you benefit more from any non-refundable credits etc. This is partly due to the fact that when you are filing your taxes in Year 1, you can't include anything from Year 2 since it hasn't happened yet. It doesn't make sense for the Government to take into account actions that may or may not happen when calculating your tax bill. There are factors where other year profit/loss can affect your tax liability, however as far as I know these are limited to businesses. Look into Loss Carry Forwarded/Back if you want to know more. Regarding the '30% simple rate', I think you are confusing something that is simple to say with something that is simple to implement.  Are we going to go change the rules on people who expected their mortgage deduction to continue? There are few ways I can think of that are more sure to cause home prices to plummet than to eliminate the Mortgage Interest Deduction. What about removing Student Loan Interest? Under a 30% 'simple' rate, what tools would the government use to encourage trade in specific areas? Will state income tax deduction also be removed? This is going to punish those in a state with a high income tax more than those in states without income tax. Those are all just 'common' deductions that affect a lot of people, you could easily say 'no' to all of them and just piss off a bunch of people, but what about selling stock though? I paid $100 for the stock and I sold it for $120, do I need to pay $36 tax on that because it is a 'simple' 30% tax rate or are we allowing the cost of goods sold deduction (it's called something else I believe when talking about stocks but it's the same idea?) What about if I travel for work to tutor individuals, can I deduct my mileage expenses? Do I need to pay 30% income tax on my earnings and principal from a Roth IRA? A lot of people have contributed to a Roth with the understanding that withdrawals will be tax free, changing those rules are punishing people for using vehicles intentionally created by the government. Are we going to go around and dismantle all non-profits that subsist entirely on tax-deductible donations? Do I need to pay taxes on the employer's cost of my health insurance? What about 401k's and IRA's? Being true to a 'simple' 30% tax will eliminate all 'benefits' from every job as you would need to pay taxes on the value of the benefits. I should mention that this isn't exactly too crazy, there was a relatively recent IRS publication about businesses needing to withhold taxes from their employees for the cost of company supplied food but I don't know if it was ultimately accepted. At the end of the day, the concept of simplifying the tax law isn't without merit, but realize that the complexities of tax law are there due to the complexities of life. The vast majority of tax laws were written for a reason other than to benefit special interests, and for that reason they cannot easily be ignored. Legally, do I have anything to worry about from having an incorrectly filed W-4? What you did wasn't criminal. When you submitted the form it was correct. Unfortunately as your situation changed you didn't adjust the form, that mistake does have consequences. Is there anything within my rights I can do to get the company to take   responsibility for their role in this situation, or is it basically my   fault? It is basically your fault. The company needs a w-4 for each employee. They will use that W-4 for every paycheck until the government changes the regulation, or your employment ends, or you submit a new form. Topic 753 - Form W-4 – Employee's Withholding Allowance Certificate If an employee qualifies, he or she can also use Form W-4 (PDF) to   tell you not to deduct any federal income tax from his or her wages.   To qualify for this exempt status, the employee must have had no tax   liability for the previous year and must expect to have no tax   liability for the current year. However, if the employee can be   claimed as a dependent on a parent's or another person's tax return,   additional limitations may apply; refer to the instructions for Form   W-4. A Form W-4 claiming exemption from withholding is valid for   only the calendar year in which it is filed with the employer. To   continue to be exempt from withholding in the next year, an employee   must give you a new Form W-4 claiming exempt status by February 15 of   that year. If the employee does not give you a new Form W-4,   withhold tax as if he or she is single, with no withholding   allowances. However, if you have an earlier Form W-4 (not claiming   exempt status) for this employee that is valid, withhold as you did   before. (I highlighted the key part) Because you were claiming exempt they should have required you to update that form each year. In your case that may not have applied because of the timing of the events. When do you submit a new form? Anytime your situation changes. Sometimes the change is done to adjust withholding to modify the amount of a refund. Other times failure to update the form can lead to bigger complication: when your marital status changes, or the number of dependents changes. In these situations you could have a significant amount of under-withheld, which could lead to a fine later on. As a side note this is even more true for the state version of a W-4. Having a whole years worth of income tax withholding done for the wrong state will at a minimum require you to file in multiple states, it could also result in a big surprise if the forgotten state has higher tax rate. Will my (now former) employee be responsible for paying their portion of the taxes that were not withheld during the 9 months I was   full-time, tax Exempt? For federal and state income taxes they are just a conduit. They take the money from your paycheck, and periodically send it to the IRS and the state capital. Unless you could show that the pay stubs said taxes were being withheld, but the w-2 said otherwise; they have no role in judging the appropriateness of your W-4 with one exception. Finally, and I am not too hopeful on this one, but is there anything I   can do to ease this tax burden? I understand that the IRS is owed no   matter what. You have one way it might workout. For many taxpayers who have a large increase in pay from one year to the next, they can take advantage of a safe-harbor in the tax law. If they had withheld as much money in 2015 as they paid in 2014, they have reached the safe-harbor. They avoid the penalty for under withholding. Note that 2014 number is not what you paid on tax day or what was refunded, but all your income taxes for the entire year. Because in your case your taxes for the year 2014 were ZERO, that might mean that you automatically reach the safe-harbor for 2015. That makes sense because one of the key requirements of claiming exempt is that you had no liability the year before. It won't save you from paying what you owe but it can help avoid a penalty. Lessons "Strangely enough, you have a wash sale, but, for the fact that you sold the shares and then more than 30 days passed, you can take the loss.  I mistakenly used the phrase ""and ended the year with no shared of the stock"" elsewhere, and was corrected, as one can sell at a loss up to 12/31, and have until the end of January to create a wash condition.  In your case, the facts in June combined with you ending the year with no shares removes any doubt, a wash sale, but one that's fully closed out.  Note - while Vicky's answer is correct, it should go on to say that once the stock is not owned for 30 days, the wash sale loss is permitted." "You have a sequence of questions here, so a sequence of answers: If you stopped at the point where you had multiple wins with a net profit of $72, then you would pay regular income tax on that $72. It's a short term capital gain, which does not get special tax treatment, and the fact that you made it on multiple transactions does not matter. When you enter your next transaction that takes the hypothetical loss the question gets more complicated. In either case, you are paying a percentage on net gains.  If you took a two year view in the second case and you don't have anything to offset your loss in the second year, then I guess you could say that you paid more tax than you won in the total sequence of trades over the two years. Although you picked a sequence of trades where it does not appear to play, if you're going to pursue this type of strategy then you are likely at some point to run into a case where the ""wash sale"" rules apply, so you should be aware of that.  You can find information on this elsewhere on this site and also, for example, here: http://www.marketwatch.com/story/understanding-the-wash-sale-rules-2015-03-02  Basically these rules require you to defer recording a loss under some circumstances where you have rapid wins and losses on ""substantially identical"" securities. EDIT A slight correction, you can take part of your losses in the second year even if you have no off-setting gain.  From the IRS: If your capital losses exceed your capital gains, the amount of the excess loss that you can claim on line 13 of Form 1040 to lower your income is the lesser of $3,000, ($1,500 if you are married filing separately)" Once the business is shut down, you'll need to show that the corporation is in bankruptcy and the amounts are unrecoverable. You can then report it as investment loss. I suggest talking to a tax adviser (EA/CPA licensed in your State), and maybe an attorney, on what the specific technical details are. No such account exists as capital gains aren't realized until holdings are sold. For example: OR  Both scenarios would result in you owing the appropriate taxes on a $40 gain from the dividends.   The $100 gain or $100 loss that isn't realized (you haven't sold the stock) isn't accounted for until the year of sale.