Can Per Diem deductions include family travel, meals and housing?
You cannot deduct anything. Since you're actually moving, your tax home will move with you. You can only deduct the moving expenses (actual moving - packing, shipping, and hotels while you drive yourself there).
"I'm not a tax professional, but as I understand it, you are not expected to commute from San Francisco to Boston.  :) If your employer has not provided you with an external office, then yes, you have very likely met the ""convenience of the employer"" test. However, to take the home office deduction, there are many requirements that have to be met. You can read more at the Nolo article Can You Deduct Your Home Office When You're an Employee? (Thanks, keshlam) The home office deduction has many nuances and is enough of an IRS red flag that you would be well-advised to talk to an accountant about it.  You need to be able to show that it is exclusively and necessarily used for your job. Another thing to remember: as an employee, the home office deduction, if you take it, will be deducted on Schedule A, line 21 (unreimbursed employee expenses), among other Miscellaneous Deductions.  Deductions in this section need to exceed 2% of your adjusted gross income before you can start to deduct.  So it will not be worth it to pursue the deduction if your income is too high, or your housing expenses are too low, or your office is too small compared to the rest of your house, or you don't itemize deductions." A per diem payment is a cost of doing business for the company, not for you. They can claim it (probably); you can't (definitely). "It depends on what the ""true"" reason for the trip is.  If you decide to deduct the trip as a business expense, then during an audit you will be asked why you had to go there. If there was nothing accomplished via the travel (that is, you worked from the hotel, met with no clients, visited no tradeshows, etc) then the expense is unlikely to be allowed. Yes, on a business trip you can do sightseeing if you wish (though you can't deduct any sightseeing specific expenses, like admission to a tourist attraction), but if you are just working while on vacation, then the trip itself is not deductible, since there was no business benefit to traveling in the first place." As I understand it... Generally housing can't be considered a business expense unless taken at your employer's explicit direction, for the good of the business rather than the employee. Temporary assignment far enough from you home office that commuting or occasional hotel nights are impractical,  maybe.  In other words, if they wouldn't be (at least theoretically) willing to let you put it on an expense account, you probably can't claim it here. You can always reduce the income by the direct expenses required to earn it, and figure out whether it is ultimately a net profit or loss.   The net profit is taxable income.  The loss may be tax deductible if the underlying thing is tax deductible.    For the book, the $50 revenue required a $100 expense, so that's a $50 net loss.  You don't owe any income tax since it's a loss.  You could take the loss as a tax deduction if you have a business trading books, or if buying the book would be tax deductible for some reason.  Note that in the latter case you can only deduct the $50 not the $100.  For the airline ticket, it is to compensate you for the losses you took as a result if the delayed flight. So you tally up the $22 meal you had in the airport waiting for news, the $110 on the motel room you rented or forfeited, any other way you can peg a cash value to any losses you took.  Total them up, again, a net loss is only deductible if the travel is already deductible. Note that if the actual expenses (book, flight) were tax deductible for some reason, the cash-back reduces the amount of your tax deduction, so it has the same effect as the sale/gift being taxable income. "I haven't dealt with this kind of thing in any way, but I found some quotes from IRS publications which I think are relevant and hopefully help. Your scenario sounds to me like a Qualified Tuition Reduction as described in Publication 970 Tax Benefits for Education. It appears the rules are different for graduate study as opposed to pre-graduate work, though I don't see anything about any dollar amount limit. There are various requirements and exceptions, so hopefully reading through that section of the publication can help you understand whether the benefit is supposed to be taxable. If taxable, it should show up on your W-2 like any other income: Any tuition reduction that is taxable should be included as wages on your Form W-2, box 1. Report the amount from Form W-2, box 1, on line 7 (Form 1040 or Form 1040A) or line 1 (Form 1040EZ).  It doesn't appear that there is any special designation or box for the tuition reduction as opposed to ""normal"" work, it just is income that's been earned like any other. If you need guidance on how much of the income is for ""normal"" work and how much is for the tuition reduction, you probably need to see if you can figure it out from her pay stubs, or contact the university's HR department. Well, looking through the credits I see in Publication 970, there appear to be two possible credits: The ""American opportunity credit"" section, under ""No double benefit allowed"", says things like (my emphasis added): You can't do any of the following.  ⋮ My understanding from reading through the section is that expenses are only excluded if they were tax-free, so that there can't be a double-dipping of benefits. If they're included as taxable income, I think they would count under your second interpretation, that the employer paid them like any other income, and your wife spent them as educational expenses just like other students, and they would qualify for educational credits. In fact, it explicitly states: Don't reduce qualified education expenses by amounts paid with funds the student receives as: Which sure sounds to me that anything that counts as W-2 Box 1 ""Wages"" would be payments received that then the expenses were logically paid separately from. The other credit, the ""Lifetime Learning Credit"", appears to use identical language (No double benefits; and don't reduce by wages). Obviously this is just from my looking through Publication 970; there may be more nuances here and for ""real"" advice you may want to speak more to the university HR department (who perhaps have dealt with this before) and/or a real tax advisor. You might also see if you can get any sort of a ""receipt"" or even a Form 1098-T from the university of what amount was paid on your wife's behalf, to help document it is truly that she was just paid more wages and spent them on classes as far as tax law is concerned." Essentially obamacare act is forcing me NOT to claim my sister as my dependent (although I provide > 51% for her).  No, that's not what it's doing. It's forcing you (or her) to get insurance. So, as a big sister I can provide for her, but NOT claim her as my dependent. Do I understand everything correctly?  The exemption (that gave you that $1K back) can only be claimed by you, she cannot claim it. So by not claiming her you're giving that up. Her medical bills will probably be on you as well, so it would be in your best interest to have her insured. If you want to dump her on the taxpayer in case of a medical emergency - then yes, it will cost you the tax benefit of the additional exemption and the HOH deduction (depending on your tax rates, probably a couple of thousands of dollars). Either way you'll pay. "I can say that I got X dollars from an account like ""Income:Benefits""... but where do I credit that money to? ""Expenses:Groceries"" Yes doesn't feel right, since I never actually spent that money on food,  You did, didn't you? You got food. I'm guessing there's an established convention for this already?  Doubt it. Established conventions in accounting are for businesses, and more specifically - public companies. So you can find a GAAP, or IFRS guidelines on how to book benefits (hint: salary expense), but it is not something you may find useful in your own household accounting. Do what is most convenient for you. Since it is a double-booking system - you need to have an account on the other side. Expenses:Groceries doesn't feel right? Add Expenses:Groceries:Benefits or Expenses:Benefits or whatever. When you do your expense and cash-flow reports - you can exclude both the income and the expense benefits accounts if you track them separately, so that they don't affect your tracking of the ""real"" expenses." During World War II, the United States (US) instituted wage and price controls.  To attract better employees, companies would offer benefits to get around salary limits.  Health insurance was one of the more successful benefits.   At that time, income taxes were newer and there were many ways to evade them.  Companies could generally deduct expenses.  So at that time, health care was deductible because everything was.  And at that time, only wages were taxable compensation from employer to employee.   Since that time, many other benefits have become non-deductible for employers, e.g. housing or the reduced deduction for meals and entertainment.  But health care is generally regarded as different, as a necessity.  While everyone needs to eat, not everyone needs to eat at a $100 a meal restaurant.  People who need expensive health care really need it.  People who eat expensive food just prefer it.   And of course, health care is more intermittent where food is relatively consistent.  You don't need ten thousand calories one day and zero the next.  But some families have no health care expenses in a year while another might have cancer or a pregnancy.  Note that medical care expenses can be deducted for individuals if they are large enough in aggregate and you itemize.   And of course both businesses and workers have incentives to maintain the current system with deductibility.  Health insurance is a common benefit.  Housing is not (although it's worth noting that travel housing and meals are deductible).  So there have been few people impacted by making housing taxable while many people would be impacted by taxable health insurance.   You can deduct health insurance costs if self-employed.  It's also not true that health insurance is the only benefit with preferential tax treatment.  Retirement and child care are also deductible.  Even meals and housing can be deducted in certain circumstances.  The complex rules about what and how much is deductible.   There have been rumbles about normalizing the tax treatment of health insurance and medical care, but there is a lot of opposition.  Insurance companies oppose making all healthcare expenses deductible, as that reduces their effective benefit.  They would prefer only insurance premiums be deductible.  Traditionally employed individuals oppose making health insurance taxable, as that would increase their taxes.  So the situation persists.  There isn't quite enough support to move in either direction, although the current compromise is economically silly. 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 Trust me, the plane ticket is the least of the expenses flying my co-worker out they will face.  His room, his meals outside of what they will serve him, etc.    he will steal every red cent he can from them because he is a filthy thief. 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. The relevant IRS publication is pub 463. Note that there are various conditions and exceptions, but it all starts with business necessity. Is it necessary for you to work from the UK? If you're working from the UK because you wanted to take a vacation, but still have to work, and would do the same work without being in the UK - then you cannot deduct travel expenses. It sounds to me like this is the case here. "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." "When you do your taxes, you have two choices for your deductions. You can take the standard deduction, or you can choose to itemize your deductions. If you itemize your deductions, you use Form 1040 Schedule A.  By looking at Schedule A, you can see the list of deductions that are itemized: On Schedule A itself, you only list a total for each of these broad categories. In some cases, this is sufficient detail. However, for certain deductions, finer detail may be required, and you may have to submit additional forms showing this detail. For example, on the medical expense line, you generally only list a total of medical expenses; details are only supplied to the IRS upon request. For noncash gifts to charity, you need to supply more details on Form 8283 if your gifts are worth more than $500.  These requirements can be found in the instructions for Schedule A. As noted by @Accumulation in the comments, the above deductions that are a part of your itemized deductions are called ""below the line"" deductions (because they are subtracted after the adjusted gross income line) and are only able to be deducted if you choose to decline the standard deduction. There are other deductions that are available whether or not you itemize. These ""above the line"" deductions are found on Form 1040 Lines 23-35. If you look at these lines on the form, you'll see the different types of deductions that are called out here. Some of these deductions require additional details on other forms; for example, the HSA deduction requires details on Form 8889.  If you have a business, your business expenses are not part of your itemized deductions at all, and do not appear on Schedule A anywhere. Instead, your business expenses get subtracted from your business's revenue, and the resulting profit (or loss) is what is reported on your Form 1040.  Different types of businesses report these expenses differently. If you have a sole proprietorship, the details of your business's expenses are reported on Schedule C. On this schedule, Part II is devoted to deductible business expenses. Take a look at Schedule C, and you'll see that Lines 8-27 are different categories of expenses that get called out on this schedule."