Visiting vacation rental with immediate family
No, you cannot deduct it. There's no business substance in such a trip, it is your vacation, and as such cannot be claimed as an expense against the rental income. You may be able to deduct the coffee you buy for the meeting with the property manager while there, but there's no way you can justify a 7-10 days vacation with your whole family as an expense to maintain the rental property. Since you will only have less than 2 weeks personal use, you won't need to prorate expenses, so you have that at least. If you and your wife are owners, your tickets might be a business expense against the rental income. 'Might' as in the IRS will be happy to audit you, seeing the kids went as well and prorating the expense as say 25% was really business, the rest, family vacation.  If this $4000 write off is the make or break for this deal, don't do it.
Government employees earn lots of airline miles if they travel frequently. However they are not allowed to use them for anything other than upgrades for themselves, you can't convert them into private travel vouchers for example. If a Govt employee gets bumped off a flight they can't even keep that money.   Because their fares are pre-negotiated on many city pair routes it will be a certain percentage of a refundable, flexible coach ticket, like 40% cheaper. However the airline miles rack up based on the class of the ticket which means they get a LOT of miles. Most private companies let their employees keep their miles and do whatever they want with them - so most of those people decide to stay in coach and keep them for a family vacation later. Oh, geez, well-regarded arguments against investing, hmm? Well, I have a couple. They're not against investing per se. They're asking about your priorities and whether you might have something better to do than inevesting: And he spake a parable unto them, saying, The ground of a certain   rich man brought forth plentifully: and he thought within himself,   saying, What shall I do, because I have no room where to bestow my   fruits? And he said, This will I do: I will pull down my barns, and   build greater; and there will I bestow all my fruits and my goods. And   I will say to my soul, Soul, thou hast much goods laid up for many   years; take thine ease, eat, drink, and be merry. But God said unto him, Thou fool, this night thy soul shall be   required of thee: then whose shall those things be, which thou hast   provided? So is he that layeth up treasure for himself, and is not   rich toward God. -- Luke 12:16-21 Christian or otherwise, there may be better things for you to do with your excess cash - indeed, with your life - than simply invest it to bring yourself more money. Many people find charitable contributions more important than spending a little more money on themselves (immediately or in the future). Of course, you will need to decide what these things are that matter to you. Perhaps you would like to contribute to traditional charities. Perhaps you would like to fund education, or a religious organization, or the Democratic Party, or the Republican Party, or the Libertarian Party, or the Green Party, or the Tea Party, or Occupy Wall Street. Perhaps you'd like to fund research into something. Perhaps you simply have friends and family that you want to make happy. Perhaps a small vacation to spend time with family is worth more to you now than the investment returns will be worth later. Moreover, note that economic decisions like this are made on the margin - it's not so much a question of whether you invest at all, but whether you should invest more or less, and spend/donate more or less. I made me great works; I builded me houses; I planted me vineyards:      I made me gardens and orchards, and I planted trees in them of all   kind of fruits:    I made me pools of water, to water therewith the   wood that bringeth forth trees:    I got me servants and maidens, and   had servants born in my house; also I had great possessions of great   and small cattle above all that were in Jerusalem before me:       I   gathered me also silver and gold, and the peculiar treasure of kings   and of the provinces: I got me men singers and women singers, and the   delights of the sons of men, as musical instruments, and that of all   sorts. So I was great, and increased more than all that were before me in Jerusalem: also my wisdom remained with me.     And whatsoever mine   eyes desired I kept not from them, I withheld not my heart from any   joy; for my heart rejoiced in all my labor: and this was my portion of   all my labor.      Then I looked on all the works that my hands had   wrought, and on the labor that I had labored to do: and, behold, all   was vanity and vexation of spirit, and there was no profit under the   sun. -- Ecclesiastes 2:4-11 Because in the long run, we're all dead. Anywho! It's all a matter of returns and risk analysis. Even spending on yourself and charitable giving can be thought in these terms (the returns are not 'more money', so they may be harder to analyze, but they're important too). If you don’t want your high-end rest house to just sit around for most of the year, only to be used during one of your rare, out-of-town family vacations, you might as well earn a profit out of it by turning it into a guesthouse. You can thank hedge funds for that.   Was looking to buy a rental and the home sold for more than asking.  This happened 3 times.   Realtor told me that they are buying all the single family homes sight unseen.  As soon as a home under 250k goes up for sale,  it's sold in my city.   Since 2011 the average home buyer has had to out offer them significantly in order to get them. "That ain't nothing.  It's really easy to get ""whipped up"" into a sense of entitlement, and forget to be grateful for what you do have.  If this house doesn't exist, what would his costs of housing be elsewhere?  Realistically.  Would landlords rent to him? Would other bankers lend him money to buy a house? Would those costs really be any better?  What about the intangible benefits like not having any landlord hassles or having a good relationship with the neighbors?  It's entirely possible he has a sweet deal here, and just doesn't make enough money.  If your credit rating is poor, your housing options really suck.  Banks won't lend you money for a house unless you have a huge ton of upfront cash.  Most landlords won't rent to you at all, because they are going to automated scoring systems to avoid accusations of racism.  In this day and age, there are lots of ways to make money with a property you own.  In fact, I believe very firmly in Robert Allen's doctrine: Never sell.  That way you avoid the tens of thousands of dollars of overhead costs you bear with every sale. That's pure profit gone up in smoke.  Keep the property forever, keep it working for you.  If he doesn't know how, learn.  To ""get bootstrapped"" he can put it up on AirBnB or other services. Or do ""housemate shares"".  When your house is not show-condition, just be very honest and relatable about the condition.  Don't oversell it, tell them exactly what they're going to get.  People like honesty in the social sharing economy.  And here's the important part: Don't booze away the new income, invest it back into the property to make it a better money-maker - better at AirBnB, better at housemate shares, better as a month-to-month renter. So it's too big - Is there a way to subdivide the unit to make it a better renter or AirBnB?  Can he carve out an ""in-law unit"" that would be a good size for him alone? If he can keep turning the money back into the property like that, he could do alright.  This is what the new sharing economy is all about.  Of course, sister might show up with her hand out, wanting half the revenue since it's half her house.  Tell her hell no, this pays the mortgage and you don't!  She deserves nothing, yet is getting half the equity from those mortgage payments, and that's enough, doggone it!  And if she wants to go to court, get a judge to tell her that.  Not that he's going to sell it, but it's a huge deal. He needs to know how much of his payments on the house are turning into real equity that belongs to him.   ""Owning it on paper"" doesn't mean you own it.  There's a mortgage on it, which means you don't own all of it.  The amount you own is the value of the house minus the mortgage owed.   This is called your equity.   Of course a sale also MINUS the costs of bringing the house up to mandatory code requirements,  MINUS the cost of cosmetically making the house presentable.   But when you actually sell, there's also the 6% Realtors' commission and other closing costs.  This is where the mortgage is more than the house is worth.  This is a dangerous situation.  If you keep the house and keep paying the mortgage all right, that is stable, and can be cheaper than the intense disruption and credit-rating shock of a foreclosure or short sale.  If sister is half owner, she'll get a credit burn also. That may be why she doesn't want to sell.  And that is leverage he has over her.  I imagine a ""Winter's bone"" (great movie) situation where the family is hanging on by a thread and hasn't told the bank the parents died.  That could get very complex especially if the brother/sister are not creditworthy, because that means the bank would simply call the loan and force a sale.   The upside is this won't result in a credit-rating burn or bankruptcy for the children, because they are not owners of the house and children do not inherit parents' debt." You have multiple things going on some of which will work in opposite directions. This is a second job for the family so that their income will be added onto of the main income. This generally means that the 2nd income has too little tax withheld. The tax tables used by employers have no way of handling this situation. This 2nd job is being started part way though the tax year, so too much in taxes is withheld. If they make 2,000 a month for 4 months that would mean 8,000 in income; but the tax tables used by the employer withhold at the $24,000 per year rate. The third issue is the great variation in the number of hours per pay period. This means that too much is withheld in checks with the most hours, and too little in the ones with the least hours. For this year you have a reprieve. As long as you make the safe-harbor levels for federal withholding, you can avoid penalties when you file next spring. To do so just make sure that the withholding of all the jobs in the family equal or exceed the total income tax for the family last year. Note this isn't equal to last years withholding, or equal to the refund last year, but the total tax you should have paid. The general advice is to set the smaller income to have 0 exemptions, and use the W-4 for the larger income to make adjustments. In the past I have done this to make sure that we make the safe-harbor level. You can make adjustments in the new year once you know what the safe harbor goal is for the rest of the year. yes. And the rentals facilitating terrorism is such a ludicrous claim at least compared to what hotels themselves do, namely rent rooms to anyone showing up with a credit card or in the lower tiers even cash. That is even easier than ABnB where at least you have to spend a few minutes to create an account.   The real terrorism risk around hospitality is hospitality being targeted or used for laundering money which is also a lot easier in a large hotel than doing it one ABnB rental unit at a time. Maybe you should consider setting up a Taxpayer Identification Number (TIN) for your business dealings as a landlord and consider providing that instead of your SSN for this type of thing. I am assuming (if this is legitimate) they want it so they can send you a 1099 as they might be obligated to do if they are claiming the rent as a business expense. Also, I'd suggest having the tenant tell their employer to contact you directly. There is no need for the tenant in this situation to also get your SSN/TIN.