Is it legal for a landlord to report a large payment to a tenant using Form 1099?
I believe it's not only legal, but correct and required. A 1099 is how a business reports payments to others, and they're required by the IRS to send them for payments of $600 or more (for miscalleneous payments like this). The payment is an expense to the landlord and income to you, and the 1099 is how that's documented (although note that if they don't send you a 1099, it's still income to you and you still need to report it as such). It's similar to getting a 1099-INT for interest payments or a 1099-DIV for dividend payments. You'll get a 1099-MISC for a miscellaneous payment. If you were an employee they'd send you a W-2, not a 1099. "It is legal.  They're probably going to give you a 1099-MISC, which is required of businesses for many cash payments over $600 in value to all sorts of counterparties.  (Probably box 3 of 1099-MISC as is typical in ""cash for keys"" situations where one is paid to vacate early)   A 1099-MISC is not necessarily pure income, but in this case, you do have money coming in.  This money isn't a return of your security deposit or a gift. The payment could possibly be construed by you as a payment to make you whole, but the accounting for this would be on you.  This is not a typical situation for IRS reporting.   However, if you are uncomfortable with potentially explaining to the IRS how you implemented advice from strangers over the internet, the safest course is to report it all as income.  Look at it this way: you did enter into a mutual contract, where you were paid consideration to release your leasehold interests in the property."
"Payment gateways such as Square do not normally withhold tax. It is up to you to pay the appropriate tax at tax time. That having been said, Square does report your payments to the IRS on a form 1099-K if your payments are large enough. According to Square, you'll get a 1099-K from them if your total payments for the year add up to $20,000 AND more than 200 transactions.  Whether or not they report on a 1099-K, you are required to pay the appropriate taxes on your income.  So now the question becomes, ""Do I have to pay income tax on the proceeds from my garage sale?"" And the answer to that question is usually not. When you sell something that you previously purchased, if you sell it for more than you paid for it, you have a capital gain and need to pay tax on that. However, generally you sell things in a garage sale at a loss, meaning that there is no tax due.  If you make more than $20,000 at your garage sale and the IRS gets a 1099-K, the IRS might be curious as to how you did that with no capital gain. So if you sell any big ticket items (a bulldozer, for example), you should keep a record of what you paid for it, so you can show the loss to the IRS in the event of an audit." "If one looks at the ""Guide to Information Returns"" in the Form 1099 General Instructions (the instructions that the IRS provides to companies on how to fill out 1099 and other forms), it says that the 1099-B is due to recipient by February 15, with a footnote that says ""The due date is March 15 for reporting by trustees and middlemen of WHFITs."" I doubt that exception applies, though it may. There's also a section in the instructions on ""Extension of time to furnish statements to recipients"" which says that a company can apply to the IRS to get an extension to this deadline if needed. I'm guessing that if you were told that there were ""complications"" that they may have applied for and been given this extension, though that's just a guess. While you could try calling the IRS if you want (and in fact, their web site does suggest calling them if you don't receive a W-2 or 1099-R by the end of February), my honest opinion is that they won't do much until mid-March anyway. Unfortunately, you're probably out of luck being able to file as early as you want to." Forms 1099 and W2 are mutually exclusive. Employers file both, not the employees. 1099 is filed for contractors, W2 is filed for employees. These terms are defined in the tax code, and you may very well be employee, even though your employer pays you as a contractor and issues 1099. You may complain to the IRS if this is the case, and have them explain the difference to the employer (at the employer's expense, through fines and penalties). Employers usually do this to avoid providing benefits (and by the way also avoid paying payroll taxes). If you're working as a contractor, lets check your follow-up questions: where do i pay my taxes on my hourly that means does the IRS have a   payment center for the tax i pay. If you're an independent contractor (1099), you're supposed to pay your own taxes on a quarterly basis using the form 1040-ES. Check this page for more information on your quarterly payments and follow the links. If you're a salaried employee elsewhere (i.e.: receive W2, from a different employer), then instead of doing the quarterly estimates you can adjust your salary withholding at that other place of work to cover for your additional income. To do that you submit an updated form W4 there, check with the payroll department on details. Is this a hobby tax No such thing, hobby income is taxed as ordinary income. The difference is that hobby cannot be at loss, while regular business activity can. If you're a contractor, it is likely that you're not working at loss, so it is irrelevant. what tax do i pay the city? does this require a sole proprietor   license? This really depends on your local laws and the type of work you're doing and where you're doing it. Most likely, if you're working from your employer's office, you don't need any business license from the city (unless you have to be licensed to do the job). If you're working from home, you might need a license, check with the local government. These are very general answers to very general questions. You should seek a proper advice from a licensed tax adviser (EA/CPA licensed in your state) for your specific case. There's nothing wrong with it. Living in a two-family house and renting the downstairs was a fairly standard path to the middle class and home ownership in the 20th century. Basically, if market conditions are good, you'll have someone else paying your mortgage. The disadvantage of the situation is that you're a landlord. So you have to deal with your tenant, who is also a neighbor. Most tenants are fine, but the occasional difficult person may come out of the woodwork. That model of achieving home ownership became less popular in the late 60's-early 70's when the law allowed two incomes to be used for mortgage underwriting. Also, as suburbanization became a national trend, absentee landlords became more common Sounds like you are in the right place at the right time, and have stumbled into a good deal. For every document that the IRS posts, there will be a correlating instructions page. This would be the instructions for the 1099-B, here. Furthermore, as you will be reporting this on Form 8949, as a substitute for previously used Schedule D; instructions are here.This article explains that the best course of action is to donate the shares as the cost basis would switch to FMV (fair market value) of the assets today. But as this did not happen, I would recommend contacting the purchasing company directly. Being a share holder, and by purchasing the shares from the source, the accounting department should still have recorded the date of purchase along with the price sold. It may take effort to prove who you are, but if their accounting records are well documented, this will not be an issue.  If nothing else, claim a 100% capital gain on the entirety of the sale, and pay the tax. That is stated here. Because a paying down a liability and thus gaining asset equity is not technically an expense, GnuCash will not include it in any expense reports. However, you can abuse the system a bit to do what you want.  The mortgage payment should be divided into principle, interest, and escrow / tax / insurance accounts. For example: A mortgage payment will then be a split transaction that puts money into these accounts from your bank account: For completeness, the escrow account will periodically be used to pay actual expenses, which just moves the expense from escrow into insurance or tax. This is nice so that expenses for a month aren't inflated due to a tax payment being made: Now, this is all fairly typical and results in all but the principle part of the mortgage payment being included in expense reports. The trick then is to duplicate the principle portion in a way that it makes its way into your expenses. One way to do this is to create a principle expense account and also a fictional equity account that provides the funds to pay it: Every time you record a mortgage payment, add a transfer from this equity account into the Principle Payments expense account. This will mess things up at some level, since you're inventing an expense that does not truly exist, but if you're using GnuCash more to monitor monthly cash flow, it causes the Income/Expense report to finally make sense. Example transaction split: "(Insert usual disclaimer that I'm just a random guy on the Internet, not any kind of certified tax professional.) But once I withdraw the money, how is that money taxable? If I'm understanding your situation correctly, you want to look at the instructions for form 8889, under Excess Employer Contributions. It simply says, ""If the excess was not included in income on Form W-2, you must report it as 'Other income' on your tax return."" There doesn't look to be any particular wording beyond that, so I'd just put it on Form 1040 Line 21 Other Income, and label the line really specifically like ""Excess Employer Contributions distributed from HSA"". Also there is no mention of whether any FICA taxes (social security and Medicare) apply to these amounts. You say that this was entirely contributed by the employer. But even for cases where one contributes directly through payroll with an optional pre-tax deduction, this is usually implemented as a ""salary reduction agreement"" where the company is actually paying less money in salary (and thus less showing up on the W-2) and just contributing to the HSA account instead. It's listed on the 8889 as an ""Employer Contribution"", even if in fact one sees it as a deduction on one's pay stub. In either case, since the company didn't pay you the money as salary (and merely contributed to the HSA instead), I wouldn't expect any FICA taxes to be owed on it. The fact that the IRS wants it listed under ""Other income"" instead of ""Wages"" also implies to me that it doesn't count as salary that needs FICA taxes. Presumably, if people abused this in some way (like getting their employer to deliberately over-contribute each year and getting a refund in some sort of crazy scheme to try to reduce their SS taxes) the government would get rather upset and probably call it some sort of tax evasion. But for the amounts involved here, particularly as you're following the instructions listed, I just wouldn't worry about it. Assuming that I withdraw excess contribution and report everything on Form 8889 and Form 1040, is there any further action required from my previous employer? It's your HSA, so I wouldn't think so. Since the eligibility for HSAs is based on what you do, and not what they do (you could, for instance, get covered by a different HDHP and they wouldn't be notified nor really care), I don't think they have anything more to do with it. Also I am not sure how to calculate amount of interest attributable to excess contribution. I have only around $0.20 of total interest this year. The bank holding the HSA could probably help with that, as I'd expect it to be a normal part of the excess contribution withdrawal process. If not, I'd just make a reasonable effort based on the interest rate, amount involved, and number of days that the excess was in the account. Also keep in mind that in general when filing taxes, anything under $0.49 can round to $0. At some point, one can only be ""as honest as the law allows""." As littleadv says, if you're a sole proprietorship, you don't need to file a 1099 for money you pay yourself. You certainly will need to file a schedule C or schedule E to report the income. And don't forget SE to pay social security taxes on the income if you made a profit. If your company is a corporation, then -- I'm not a tax lawyer here, but I think the  corporation would need to file a 1099 for the money that the corporation pays to you. Assuming that the amount is above the threshold that requires a 1099. That's normally $600, but it's only $10 for royalties.