Selling a car with a lien
You could have the buyer go to the bank with you so that he can get evidence that the loan will be paid in full and that the lien will be lifted. The bank won't sign over the title (and lift the lien) until the loan is paid back in full. DMV.org has a pretty good section about this. (Note: not affiliated with the actual DMV) Selling to a Private Party Though more effort will be required on your part, selling a car with a   lien privately could net you a higher profit. Here are a few things   you'll need to consider to make the process easier:  Include the   details of the lien in your listing. You'll list an advertisement for   your car just as you would any other vehicle, with the addition of the   lien information that buyers will need so as to avoid confusion.  Sell   in the location of the lienholder, if possible. If the bank or   financial institution holding the lien is located in the area you're   trying to sell, this will make the transaction much easier. Once you   make an agreement with the buyer, you can go directly to the lender to   pay off the existing lien. Ownership can then be transferred in person   from the financial institution to the buyer.  Consider an escrow   service. If the financial institution isn't in your area, an escrow   service can help to ensure a secure transaction. An escrow service   will assume responsibility for receiving payments from the buyer and   will hold the title until the purchase is complete. Advantages of an   escrow service include: Payoff services, which will do most of the   work with the financing institution for you. Title transfer services,   which can help to ensure a safe and legitimate transaction and provide   the necessary paperwork once the sale is complete.
Contact the lien holder (the bank) and they'll have a procedure for you. Usually, you complete the transaction at the bank after agreeing on the purchase price: you will cut a check to the bank to pay off the loan, and then write a second check to the seller for whatever extra amount should go to him. The bank will handle the paperwork for transferring the title of the car to your name. Obviously, under no circumstances should you give all the money to the seller in the hopes that he pays off the loan. You need to follow the lender's procedures because they hold the title to the car and must be the ones to transfer it to you. Banks do this type of transaction all the time. Just call them and ask about how to proceed. Are you in the United States? Is there some sort of written agreement that the money your parents paid into the house is a loan that will be paid back?  I assume the deed to the home is in your name, and your parents do not have a lien on the property in any way? In the United States provided there is no lien and your parents are not also on the mortgage, that home is 100% yours. Now I would argue you still owe your parents money, but absent some sort of contract it sounds like an interest free loan that you'll pay back at a rate of 500$/month.  Your parents could attempt to sue you and if this happens I recommend you find a real estate attorney. It's unlikely that they would win the case since there's no paperwork and even if there was it is unlikely to hold up since it so strongly favors them ( your parents ).  Now if your parents are listed on the mortgage or somehow have a lien on the house, you have a bigger issue as they technically own (or at least have an interest in) part of the property and when you decide to sell the house you would have to involve them. "I'm going to look just at purchase price. Essentially, you can't always claim the whole of the purchase price (or 95% your case) in the year (the accounting period) of purchase, but you get a percentage of the value of the car each year, called writing down allowance, which is a capital allowance. It is similar to depreciation, but based on HRMC's own formula. In fact, it seems you probably can claim 95% of the purchase price, because the value is less than £1000. The logic is a bit involved, but I hope you can understand it. You could also claim simplified expenses instead, which is just based on a rate per mile, but you can't claim both. Note, by year I mean whatever your account period is. This could be the normal financial year, but you would probably have a better idea about this. See The HMRC webpage on this for more details.  The big idea is that you record the value of any assets you are claiming writing down allowance on in one of a number of pools, that attract the same rate of writing down allowance, so you don't need to record the value of each asset separately. They are similar to accounts in accounting, so they have an opening balance, and closing balance. If you use an asset for personal use, it needs a pool to itself. HRMC call that a single asset pool. So, to start with, look at the Business Cars section, and look at the Rates for Cars section, to determine the rate you can claim. Each one links to a further article, which gives more detail if you need it. Your car is almost certainly in the special rate category. Special rate is 8% a year, main rate is 18%, and First year allowance is essentially 100%. Then, you look at the Work out what you can claim article. That talks you through the steps. I'll go through your example. You would have a pool for your car, which would end the account period before you bought the vehicle at zero (step 1). You then add the value of the car in the period you bought it (Step 2). You would reduce the value of the pool if you dispose of it in the same year (Step 3). Because the car is worth less than £1,000 (see the section on ""If you have £1,000 or less in your pool""), you would normally be able to claim the whole value of the pool (the value of the car) in the first accounting period, and reduce the value of the pool to zero. As you use the car for personal use, you only claim 95% of the value, but still reduce the pool to zero. See the section on ""Items you use outside your business"". This £1000 is adjusted if your accounting period lasts more or less than 12 months. Once the pool is down to zero that it you don't need to think about it any more for tax purposes, apart from if you are claiming other motoring expenses, or if you sell it.  It gets more complicated if the car is more expensive. I'll go through an example for a car worth £2,000.  Then, after Step 3, on the year of purchase, you would reduce the value of the pool by 8%, and claim 95% of the reduction. This would be a 160 reduction, and 95%*160 = 152 claim, leaving the value of 1860 in the pool. You then follow the same steps for the next year, start with 1840 in the pool, reduce the value by 8%, then claim 95% of the reduction. This continues until you sell or dispose of the car (Step 3), or the value of the pool is 1000 or less, then you claim all of it in that year. Selling the car, or disposing of the car is discussed in the  Capital allowances when you sell an asset article. The basic idea is that if you have already reduced the value of the pool to zero, the price you sell the car for is added you your profits for that year (See ""If you originally claimed 100% of the item""), if you still have anything in the pool, you reduce the value of the pool by the sale value, and if it reduces to below zero (to -£200, say), you add that amount (£200, in this case), to your profits. If the value is above zero, you keep applying writing down allowances. In your case, that seems to just means if you sell the car in the same year you buy it, you claim the difference (or 95% of it) as writing down allowance, and if you do it later, you claim the purchase price in the year of purchase, and add 95% of the sale price to your profits in the year you sell it. I'm a bit unclear about starting ""to use it outside your business"", which doesn't seem to apply if you use it outside the business to start with.   You can claim simplified expenses for vehicles, if you are a sole trader or partner, but not if you claim capital allowances (such as writing down allowances) on them, or you include a separate expense in your accounts for motoring expenses. It's a flat rate of 45p a mile for the first 10,000 miles, and 25p per mile after that, for cars, and 24p a mile for motorcycles. See the HRMC page on Simplifed Mileage expenses for details. For any vehicle you decide to either claim capital allowances claim running costs separately, or claim simplified mileage expenses, and ""Once you use the flat rates for a vehicle, you must continue to do so as long as you use that vehicle for your business.you have to stick with that decision for that vehicle"".  In your case, it seems you can claim 95% of the purchase price in the accounting period you buy it, and if you sell it you add 95% of the sale price to your profits in that accounting period. It gets more complicated if you have a car worth more than £1000, adjusted for the length of the accounting period. Also, if you change how you use it, consult the page on selling selling an asset, as you may have disposed of it. You can also use simplified mileage expenses, but then you can't claim capital allowances, or claim running costs separately for that car. I hope that makes sense, please comment if not, and I'll try to adjust the explanation." Even if you avoid the issue of the auto dealer wanting to limit the abuse of their policy, you have to realize that the discount they give is 25% off of some stated price. It might be 25% off the sticker. They don't want to lose money, the 25% represents the haggling they avoid by selling to the employee. This means the discount might not be as large as you imagine, because you wouldn't have paid sticker if you had purchased the vehicle on your own. The other issue you will have to deal with is taxes and registration. When your friend drives the car off the lot, the car will have to be registered with the state. Then they will have to sell the car to you, and that transaction will have to be done though the state, for a price. Then you will sell it to somebody else. These transaction fees will cut into your profits.  It is likely that when the potential purchaser runs a VIN check through a service it will show multiple owners, which can cut the estimated resale value. The manufacturer will also have to be notified so that all the relevant warranty coverage is still intact.  The question is for that final sale: can you offer enough discount compared to the new car dealer? and still make enough profit to be worth the hassle? California bankruptcy law requires disclosure of any gift made by the person declaring bankruptcy in the past 12 months, and any asset transfers in the past 2 years (with a couple of minor exceptions). This would most certainly include the car, if it is regifted back to you. Such a claim would likely be considered fraudulent, though this would be a matter for the lawyers and bankruptcy trustee in question. There's a blog which you may wish to check out, the California Bankruptcy Blog, which has a specific entry on gifts. Now, there is a specific exemption for automobiles, but only up to a total of $2725. Legally, I believe there's nothing you can do here. If the $10K was a loan, it will be discharged in bankruptcy. If it was a gift, it'll have to be declared and the car will have to be sold. If regifted or transferred, it must be declared and will likely (but not definitely) be determined as an invalid disposal of assets. Either you or your family member will have to discuss this with a bankruptcy lawyer. I'm sorry your generous act is likely to get tangled up here. :( Canada does not have tax lien certificates. Instead, they do tax deed sales.  Because the process is much further along, often involving local sheriffs, it is much closer to a U.S. foreclosure sale/auction process than a tax lien as you are likely thinking.  The laws and processes vary by province as well, so you'll want to contact the provincial government tax offices to get the details. I don't think there's much you can do. Losses from the sale of personal-use automobiles (used for pleasure, commuting, etc) are not deductible as capital losses.  See IRS Tax Topic 409, end of the first paragraph.  The expenses you incurred in owning and operating the car (insurance, fuel, maintenance, service plans, etc) are not deductible either. If you used it partly for business, then some of your expenses might be deductible; see IRS Tax Topic 510.  This includes depreciation (decline in value), but only according to a standard schedule; you don't generally just get to deduct the difference between your buying and selling price.  Also, you'd need to have records to verify your business use.  But anyway, these deductions would apply (or not) regardless of whether you sell the car. You don't get your sales tax refunded when you resell the vehicle.  That's why it's a sales tax, not a value-added tax.  Note, however, that if you do sell it, the sales tax on this new transaction will be the buyer's responsibility, not yours. You do have the option on your federal income tax return to deduct the state sales tax you paid when you bought the car; in fact, you can deduct all the sales taxes you paid in that year.  (If you have already filed your taxes for that year, you can go back and amend them.)  However, this takes the place of your state income tax deduction for the year; you can't deduct both.  See Tax Topic 503.  So this is only useful if your sales taxes for that year exceeded the state income tax you paid in that year.  Also, note that state taxes are not deductible on your state income tax return.  Again, this deduction applies whether you sell the car or not. It looks to me like this is a 'call an attorney' situation, which is always a good idea in situations like this (family legal disputes).  But, some information. First off, if your family is going to take the car, you certainly won't need to make payments on it any more at that point, in my opinion.  If the will goes through probate (which is the only way they'd really be able to take it), the probate judge should either leave you with the car and the payments, or neither (presumably requiring the family to pay off the loan and settle your interest in the car).  Since the car has negative net value, it seems unlikely that the probate judge would take the car away from you, but who knows.  Either way, if they do take the car away from you, they'll be doing you a service: you have a $6,000 car that you owe $12,000 on.  Let them, and walk away and buy another car for $6,000. Second, I'm not sure they would be allowed to in any event.  See the Illinois DMV page on correcting titles in the case of a deceased owner; Illinois I believe is a joint tenancy state, meaning that once one owner dies, the other just gets the car (and the loan, though the loan documents would cover that).  Unless you had an explicit agreement with your grandfather, anyway. From that page: Joint Ownership A title in the names of two or more persons is considered to be in joint tenancy. Upon the death of one of them, the surviving joint tenant(s) becomes the owner(s) of the vehicle by law. Third, your grandfather can fix all of this fairly easily by mentioning the disposition of the car and loan in his will, if he's still mentally competent and wishes to do so.  If he transfers his ownership of the car to you in the will, it seems like that would be that (though again, it's not clear that the ownership wouldn't just be yours anyway). Finally, I am not a lawyer, and I am not your lawyer, so do not construe any of the text of this post as legal advice; contact a lawyer.