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.
What you haven't mentioned is the purchase risk.  You say that she will buy but then say you will be on the loan. If you are on the loan, essentially you will be purchasing a rental property and renting to your mother.  So that is the analysis you need to consider. You need to be financially able to take on this purchase and be willing to be a landlord. The ten year timeline looks good on paper. This may not be realistic, especially with an aging parent.  What if after 4 years, she can't stay in that condo?  What renting buys is flexibility. If she needs money for any reason, it is not tied up in an asset and unavailable. She is able it move if necessary. If she won't need the money, she should buy in cash. That, by far, gives her the best deal. More possible considerations: Comparability with other properties.  Maybe properties that rent for $972 have more amenities than this one (parking, laundry, yard, etc) or are in better repair.  Or maybe the $972 property is a block closer to campus and thus commands 30% higher rent (that can happen).  Condition of property.  You know nothing about this until you see it.  It could be in such bad shape that you can't legally rent it until you spend a lot of money fixing it.  Or it may just be run down or outdated: still inhabitable but not as attractive to renters, leading to lower rent and/or longer vacancy periods.  Do you accept that, or spend a lot of money to renovate? Collecting the rent.  Tenants don't necessarily always pay their rent on time, or at all.  If a tenant quits paying, you incur significant expenses to evict them and then find a new tenant, and all the while, you collect no rent. There could be a tenant in place paying a much lower rent.  Rent control or a long lease may prevent you from raising it.  If you are able to raise it, and the tenant doesn't want to pay, see above. Maintenance and more maintenance.  College students could be hard on the property; one good kegger could easily cause more damage than their security deposits will cover. Being near a university doesn't guarantee you an easy time renting it.  It suggests the demand is high, but maybe the supply is even higher.  Renting to college students has additional issues.  They are less likely to have incomes large enough to satisfy you that they can pay the rent.  Are you willing to deal with cosigners?  If a student quits paying, are you willing to try to collect from their cosigning parents in another state?  And you'll probably have many tenants (roommates) living in the house.  They will come and go separately and unexpectedly, complicating your leasing arrangements.  And you may well get drawn in to disputes between them. "You will need to see a tax expert. Your edited question includes the line For the short term, we will be ""renting"" it to my wife's grandmother at a deep discount. According to the instructions for schedule E If you rented out a dwelling unit that you also used for personal   purposes during the year, you may not be able to deduct all the   expenses for the rental part. “Dwelling unit” (unit) means a house,   apartment, condominium, or similar property. For each property listed on line 1a, report the number of days in the   year each property was rented at fair rental value and the number of   days of personal use. A day of personal use is any day, or part of a day, that the unit was   used by: I have no idea how this will work for Schedule C." "The first issue you'll find is that if you aren't going to immediately live in the house as a primary residence, this property counts as a ""second home"" or ""investment property"". You'll generally pay a higher interest rate, have a larger down payment, and qualify for less government-backed programs/incentives/subsidies than you would otherwise. The lending criteria on such properties is always more strict - and generally more costly - than an equivalent primary residence. Lenders won't really care that in 10 years you or your parents plan to move in - you can't be held to that, so they'll generally ignore that plan entirely. On a related note, you should be aware that insurance for the property will also generally cost more, but you'd need to get quotes to determine if that is at all significant in your situation. You'll need to talk with a few potential lenders, but from a first read it sounds like it would be best ""storied"" like so: you and your parents want to buy a 2nd home or vacation home, which you'll share the use of (vacations, etc, and being converted to a primary residence later). It'll need to be clear what plan to use the property for - if you intend to rent out the home in the interim years then instead make that clear and state it will be an investment home; if it is what you are planning it might make it easier, as expected rent for the property will be considered. Saying you want a mortgage for a home no one will live in for a decade probably isn't a good idea, as a general plan anyway. Either way, this can be called a ""joint mortgage"". When I was a loan officer we didn't use that term, but it's basically just a mortgage application with multiple people on it, all of whom are combined together to qualify for the loan. Everyone's income, debts, assets, and credit get included, which can work or one person's situation can cause the whole thing to collapse. From your description I think this could work for you, and one option is to set it up where only one of the parents is on the application if the other parent has problematic credit situation. Note that his possibility is often restricted by local law, so it may not be an option for you in your jurisdiction, but worth being aware of. An alternative is you just buy the property and the parents gift you the down payment, and you list them as beneficiaries in will/trust in case something happens to you before they retire, but I don't know if that would make any sense in your situation. This is a single applicant mortgage, and it means only you are considered as buying it, which sometimes is the only option depending on your parents current financial situation. It's usually something you try if the other option doesn't work, but it's a fallback plan. Some lenders will allow guarantors (co-signers in US parlance), but this will vary by lender and locale - often what they actually want is a joint mortgage, not really a guarantor/cosigner. Finally, you'll need to plan for what happens if things don't go as planned, regardless of what happens. What if your income changes, if either of your parents become deceased in advance of retirement, if they get a divorced from each other, or if either/both become ill or disabled and need assisted care? Planning for such unpleasant possibilities (even if they seem crazy and not going to happen in your mind right now) can save you all a tremendous amount of heart ache later on when the unexpected (including things I didn't mention) pops up." "Obviously you have done well financially in order to be able to purchase a condo for cash, presumably, without risk of your other obligations.  To put things in perspective, we are probably talking about less than $5,000 in tax savings.   If she is on the title then she is a co-owner.  Are you okay with that?  You would essentially be giving this child a 50% stake in a property without compensation.  Will your other children be okay with it? As your question stated you would prefer to not have her as an owner.  However, is it better to not have her as an owner, So I would buy the condo without her on the title and just pay the extra $100 per month in property tax.  It is probably ""small potatoes"" in comparison to your net worth. I would also only charge her at most your cost of carrying the property as rent.  While you will create income all of it (and probably more) could be written off as costs.  There should be no income tax burden created from this situation.  Your accountant can help with any paperwork that needs to be filed." "The Trustee has allowed me to act as his ""agent"", continuing to pay   bills, and take care of much of the administrative affairs for my   mother's estate since I did all of it for years before she passed   away. I was not paid for any of this work. ... The expenses were more than $30K last year, and there is still a punch list to go this year. The trust should reimburse your expenses and deduct them on the trust tax return. Since the Trust owned the property in 2015, and I will receive ownership this month, can last year's expenses incurred for the Trust be deducted again future income for my property this year?  Not exactly. The trust will file its own tax return and will report the income/loss attributed to the beneficiaries per the trust rules. What is attributed to you will flow to your Schedule E. From there you own it and if it is a passive activity where the loss is limited - you can carry it forward and offset with future gain. The trustee will have to deal with all the paperwork. Do 1099-misc forms need to be filed for the contractors who worked to get it ready for rental? It is my understanding that since 2010 (and before 2010) landlords who are not in real-estate trade or business are not required to send out 1099. But it won't hurt if you do, also. In any case - for all of these issues you should talk to a tax adviser (EA/CPA licensed in your State)." Schedule E is the form you'll use. It lists nearly all deductions you can take for a rental. TurboTax Deluxe will handle it and it includes State Filing. The Military Home owners wants to remain living in the home for 2 weeks after the closing date. You can include this provision in your contract. By putting the seller directly across the table, you can put your heads together and find win-win solutions to some issues that may arise. That's a good point. I worry that it may look bad if I go on holiday or come in whenever I want. My dad suggested I swan in and check out different businesses whenever I want.  Maybe I should do full employee hours for a week at each place or something, as opposed to just going in for a couple of hours randomly. Sorry, but I think you really do need an attorney here. This is the kind of minefield where knowing all the precedents and edge cases can make a huge difference in what you can or can't do, and a misplaced comma can make or break your case. Note that AT BEST you could sell your own interest in the house -- owning the note does not mean owning the property, it only means that they issued the note on the strength of your share of the property. And a half-interest in a single family house has little value outside the family, except to sell it to whoever owns the other half. Which is probably the best answer: Sell your half to your Aunt, if she can afford to buy it. She then gets sole control of the house, and you get the money you seem to need right now, and everyone in the family is much less stressed. Your reasoning is backwards. As others have pointed out, you cannot just decide how much you charge irrespective of the market. Let me paraphrase a little economics 101 to underline why you also should not think like this: You can see a rental property like your house (the same reasoning is usually explained with the example of hotel rooms) as a series of perishable goods. Your house represents the potential sale of the January rent (which perishes once January is over), plus the February rent etc. Your approach was to compute the total costs (all fixed and variable costs of owning that house as well as costs associated to renting specifically) and average them over the time period so that you know how much to ask at least. Assuming that you are only looking to rent it out, not sell it or let a family member live there, you can't think like this. Most of those costs that you averaged are what economists call sunk costs. You have already incurred the mortgage costs and they are not affected by your decision to rent or not to rent. These costs are irrelevant to your decision making process. You only need to think about marginal costs: those additional costs that you have when you rent but not when you don't. Look at the market prices for renting similar properties in that region and compare them with your marginal costs. As long as they are higher than your marginal costs, rent it out. This does not mean that you are sure to make profits, but it means that you are sure to make less losses than in your only alternative of not renting. "My biggest concern with this plan is that there's no going back should you decide that it is not going to work, either due to the strain on the relationship or for some other reason.   If you were borrowing from a relative in place of a mortgage or a car loan, you can always refinance, and might just pay a little more interest or closing costs from a bank.  Student loans are effectively unsecured, so your only option for a ""refinance"" would be to get a personal, unsecured loan (or borrow against existing collateral if you have it). You are going to have a tough time getting another 50k unsecured personal loan at anywhere near student-loan rates.   The other negative aspects (overall risk of borrowing from family, loss of possible tax deduction) make this plan a no-go for me. (I'm NOT saying that it's always a good idea to borrow from family for homes or cars, only that there's at least an exit plan should you both decide it was a bad idea)." Also, does anyone know of any books on doing this sort of thing, i.e. renting out half of your home to a tenant and living in the ret? Head down to your local library. Mine has a state guide for renters and another one for landlords. There will likely be a lot of Nolo Press books around there too.  You can also research the property tax on a lot; many counties run an arcGIS server that will tell you who owns a given property, what the assessed value is and the total tax bill, etc. Rent the property?? Is that a possible solution? Since selling the house is not an option and living in it isn't either, then perhaps renting it is the way to go? Since no explanation for the sister's motives is given, i'd speculate it is a mixture of emotional and financial concerns. Maybe mostly emotional. I imagine letting go of the one physical thing that has memories of you and your parents attached to it is very difficult. I don't think getting a lawyer or doing what's convenient for only your boyfriend is the way to go...But that's my own personal opinion. Clearly, he only has one close family member left alive. Creating permanent wounds in that relationship will cost more along the way. And quite frankly, if the house is owned 50-50, don't you need both owners to sign the deed to sell the house anyways? If renting is not an option, then maybe refinancing the mortgage to lower payments? Or Airbnb it only half the time? Or rent it out for events to help with payments? Or ask the sister for a little money...Not for half the mortgage, but at least a few hundred dollars to maintain the house and heat. If she is indeed concerned with the property, then maintaining it to prevent serious damagae is in her interests, no matter her income. Yeah dang. Guess it's probably written deep in the contract that this can happen and nothing is absolutely guaranteed.   Any specific experience on rental car chains? I've recently started using National and love the pick your own car experience...much faster and smoother but is more expensive (and luckily reimbursed mostly as well)