Where to deduct gambling losses?
1: Gambling losses not in excess of gambling winnings can be deducted on Schedule A, line 28.  See Pub 17 (p 201).  Line 28 catches lots of deductions, and gambling losses are one of them.  See Schedule A instructions. 2: If the Mississippi state tax withheld was an income tax (which I assume it was), then it goes on Schedule A, line 5a.  In the unlikely event it was not a state or local tax on income, but some sort of excise on gambling, then it may be deductible on line 8 as another deductible tax.  It probably is not a personal property tax, which is generally levied against the value of things like cars and other movable property but not on receipts of cash; line 7 probably is not appropriate.  The most likely result, without researching Mississippi SALT, is that it was an income tax.  See Sched A Instructions for more on the differences between the types of taxes paid. Just to be clear, these statements hold if you are not engaging in poker as a profession.  If you are engaging in poker as a business, which can be difficult to establish in the IRS' eyes, then you would use Schedule C and also report business and travel expenses.  But the IRS is aware that people want to reduce their gambling income by the cost of hotels and flights to casinos, so it's a relatively high hurdle to be considered a professional poker player.
The harvested losses are capital losses.  See this IRS page: Generally, realized capital losses are first offset against realized capital gains.  Any excess losses can be deducted against ordinary income up to $3,000 ($1,500 if married filing separately) on line 13 of Form 1040.  Losses in excess of this limit can be carried forward to later years to reduce capital gains or ordinary income until the balance of these losses is used up. This means that your harvested losses can be used to offset ordinary income --- up to $3000 in a single year, and with extra losses carried forward to future years.  It is pretty close to a free lunch, provided that you have some losses somewhere in your portfolio. This free lunch is available to anyone, but for a human, it can be quite a chore to decide when to sell what, keep track of the losses, and avoid the wash sale rules.  The advantage of robo-advisors is that they eat that kind of bookkeeping for breakfast, so they can take advantage of tax loss harvesting opportunities that would be too cumbersome for a human to bother with. "Although this has been touched upon in comments, I think the following line from the currently accepted answer shows the biggest issue: There is a clear difference between investing and gambling. The reality is that the difference isn't that clear at all. Tens of comments have been written arguing in both directions and looking around the internet entire essays have been written arguing both positions. The underlying emotion that seems to shape this discussion primarily is whether investing (especially in the stock market) is a form of gambling. People who do invest in this way tend to get relatively emotional whenever someone argues that this is a form of gambling, as gambling is considered a negative thing. The simple reality of human communication is that words can be ambiguous, and the way investors will use the words 'investments' and 'gambles' will differ from the way it is used by gamblers, and once again different from the way it's commonly used. What I definitely think is made clear by all the different discussions however is that there is no single distinctive trait that allows us to differentiate investing and gambling. The result of this is that when you take dictionary definitions for both terms you will likely end up including lottery tickets as a valid form of investment.  That still however leaves us with a situation where we have two terms - with a strong overlap - which have a distinctive meaning in communication and the original question whether buying lottery tickets is an investment. Over on investorguide.com there is an absolutely amazing strongly recommended essay which explores countless of different traits in search of a difference between investing and gambling, and they came up with the following two definitions: Investing: ""Any activity in which money is put at risk for the purpose of making a profit, and which is characterized by some or most of the following (in approximately descending order of importance): sufficient research has been conducted; the odds are favorable; the behavior is risk-averse; a systematic approach is being taken; emotions such as greed and fear play no role; the activity is ongoing and done as part of a long-term plan; the activity is not motivated solely by entertainment or compulsion; ownership of something tangible is involved; a net positive economic effect results."" Gambling: ""Any activity in which money is put at risk for the purpose of making a profit, and which is characterized by some or most of the following (in approximately descending order of importance): little or no research has been conducted; the odds are unfavorable; the behavior is risk-seeking; an unsystematic approach is being taken; emotions such as greed and fear play a role; the activity is a discrete event or series of discrete events not done as part of a long-term plan; the activity is significantly motivated by entertainment or compulsion; ownership of something tangible is not involved; no net economic effect results."" The very interesting thing about those definitions is that they capture very well the way those terms are used by most people, and they even acknowledge that a lot of 'investors' are gambling, and that a few gamblers are 'investing' (read the essay for more on that). And this fits well with the way those two concepts are understood by the public. So in those definitions normally buying a lottery ticket would indeed not be an investment, but if we take for example Vadim's operation example If you have $1000 and need $2000 by next week or else you can't have an operation and you will die (and you can't find anyone to give you a loan). Your optimal strategy is to gamble your $1000, at the best odds you can get, with a possible outcome of $2000. So even if you only have a 1/3 chance of winning and getting that operation, it's still the right bet if you can't find a better one. this can suddenly change the perception and turn 'gambling' into 'high-risk investing'." "Gambling is perhaps not well defined, but it certainly doesn't include things like reality show winnings.   However, it is possible he could deduct something for this.  If the reality show qualifies as a ""hobby"", and his expenses exceed the 2% of AGI requirement, it's possible he could deduct those airplane tickets and such.  That deduction is explained in Publication 529." Avoiding tobacco, etc is fairly standard for a fund claiming ethical investing, though it varies. The hard one on your list is loans.  You might want to check out Islamic mutual funds. Charging interest is against Sharia law.  For example: http://www.saturna.com/amana/index.shtml From their about page: Our Funds favor companies with low price-to-earnings multiples, strong   balance sheets, and proven businesses. They follow a value-oriented   approach consistent with Islamic finance principles. Generally, these   principles require that investors avoid interest and investments in   businesses such as liquor, pornography, gambling, and banks. The Funds   avoid bonds and other conventional fixed-income securities. So, it looks like it's got your list covered.  (Not a recommendation, btw. I know nothing about Amana's performance.) Edit: A little more detail of their philosophy from Amana's growth fund page: Generally, Islamic principles require that investors share in profit   and loss, that they receive no usury or interest, and that they do not   invest in a business that is prohibited by Islamic principles. Some of   the businesses not permitted are liquor, wine, casinos, pornography,   insurance, gambling, pork processing, and interest-based banks or   finance associations. The Growth Fund does not make any investments that pay interest. In   accordance with Islamic principles, the Fund shall not purchase   conventional bonds, debentures, or other interest-paying obligations   of indebtedness. Islamic principles discourage speculation, and the   Fund tends to hold investments for several years. If your dad would have won money on the slot machines(And the amount was high), the casino would have given him a W2G to fill out right there and taxes would have been deducted. However, table games including Poker does not have any such rule. You will have to account for your winnings(And losses) at the end of the year. So, it is ok if you sign that paper, as you do not owe the IRS any money yet.  You will still need to file your taxes as a non resident alien at the end of the year and attach the form W2G with it and pay your dues. The IRS Guidance pertaining to the subject.  In general the best I can say is your business expense may be deductible.  But it depends on the circumstances and what it is you want to deduct. Travel Taxpayers who travel away from home on business may deduct related   expenses, including the cost of reaching their destination, the cost   of lodging and meals and other ordinary and necessary expenses.   Taxpayers are considered “traveling away from home” if their duties   require them to be away from home substantially longer than an   ordinary day’s work and they need to sleep or rest to meet the demands   of their work. The actual cost of meals and incidental expenses may be   deducted or the taxpayer may use a standard meal allowance and reduced   record keeping requirements. Regardless of the method used, meal   deductions are generally limited to 50 percent as stated earlier.    Only actual costs for lodging may be claimed as an expense and   receipts must be kept for documentation. Expenses must be reasonable   and appropriate; deductions for extravagant expenses are not   allowable. More information is available in Publication 463, Travel,   Entertainment, Gift, and Car Expenses. Entertainment Expenses for entertaining clients, customers or employees may be   deducted if they are both ordinary and necessary and meet one of the   following tests: Directly-related test: The main purpose of the entertainment activity is the conduct of business, business was actually conducted   during the activity and the taxpayer had more than a general   expectation of getting income or some other specific business benefit   at some future time.   Associated test: The entertainment was associated with the active conduct of the taxpayer’s trade or business and occurred directly   before or after a substantial business discussion. Publication 463 provides more extensive explanation of these tests as   well as other limitations and requirements for deducting entertainment   expenses. Gifts Taxpayers may deduct some or all of the cost of gifts given in the   course of their trade or business. In general, the deduction is   limited to $25 for gifts given directly or indirectly to any one   person during the tax year. More discussion of the rules and   limitations can be found in Publication 463. If your LLC reimburses you for expenses outside of this guidance it should be treated as Income for tax purposes. Edit for Meal Expenses: Amount of standard meal allowance.   The standard meal allowance is   the federal M&IE rate. For travel in 2010, the rate for most small   localities in the United States is $46 a day. Source IRS P463 Alternately you could reimburse at a per diem rate This loss would be unrealized and, assuming you're a cash-basis tax-payer, you would not be able to take a loss on your 2014 tax return. This is similar to if you held a stock that lost 50% of its value. You wouldn't be able to claim this loss until you finally sold it.  The link that User58220 posted may come into play if you converted your UAH back to USD. The mental approach should be that you always knew the risk of gambling and it was extra money that you had (or should have had). Now think that the 'horse' race is not over and in the near future it will pick up pace against the others and be back on track.