Live in Oregon and work in Washington: Do I need to file Oregon state taxes?
Yes. Here's the answer to this question from oregon.gov: 3. I am moving into Oregon. What income will be taxed by Oregon? As an Oregon resident, you are taxed on ALL income regardless of the   source of the income. This includes, but is not limited to: You may need to pay estimated taxes if you don't have Oregon   withholding on your income. Unfortunately, you are required, but most states do have agreements with neighboring states that let the states share the collected taxes without the person having to pay double taxes. So being as this is your first tax return in your current situation, you might be wise to have a professional fill it out for you this year and then next year you can use it as a template. Additionally, I really would like to see someone challenge this across state lines taxation in court. It sure seems to me that it is a inter-state tariff/duty, which the state's are expressly forbidden from doing in the constitution.
If you have non Residency status in Canada you don't need to file Canadian tax return. To confirm your status you need to contact Canada Revenue (send them letter, probably to complete some form). Yes, you do.  You also need to file a tax return every year, and if you have more than $50k of total savings you need to declare this every year. "IRS Pub 554 states (click to read full IRS doc):  ""Do not file a federal income tax return if you do not meet the filing requirements and are not due a refund. ... If you are a U.S. citizen or resident alien, you must file a return if your gross income for the year was at least the amount shown on the appropriate line in Table 1-1 below. "" You may not have wage income, but you will probably have interest, dividend, capital gains, or proceeds from sale of a house (and there is a special note that you must file in this case, even if you enjoy the exclusion for primary residence)" No, you probably do not need to file a tax return if you received no income, and if you meet a number of other criteria. The below is copied and pasted, slightly edited, from the CRA: You must file a return for 2014 if any of the following situations   apply: You have to pay tax for 2014. We sent you a request to file a return. You and your spouse or common-law partner elected to split pension   income for 2014. See lines 115, 116, 129, and 210. You received working income tax benefit (WITB) advance payments in   2014. You disposed of capital property in 2014 (for example, if you sold   real estate or shares) or you realized a taxable capital gain (for   example, if a mutual fund or trust attributed amounts to you, or you   are reporting a capital gains reserve you claimed on your 2013   return). You have to repay any of your old age security or employment insurance   benefits. See line 235. You have not repaid all amounts withdrawn from your registered   retirement savings plan (RRSP) under the Home Buyers’ Plan or the   Lifelong Learning Plan. For more information, go to Home Buyers' Plan   (HBP) or see Guide RC4112, Lifelong Learning Plan (LLP) or You have to   contribute to the Canada Pension Plan (CPP). This can apply if, for   2014, the total of your net self-employment income and pensionable   employment income is more than $3,500. See line 222. You are paying employment insurance premiums on self-employment and   other eligible earnings. See lines 317 and 430. In general, you will want to file a tax return even if none of the above applies. You could, for example, claim a GST/HST credit even with no income. Now, if you receive any income at all, you are going to have to pay taxes, which means you are obligated to file a tax return. If sufficient taxes were deducted from your paycheque, you are still obligated to file a tax return. However, you will not have to pay penalties if you file late, even if you file very late, at least not until the CRA sends you a request to file. But be aware, you won't likely be able to tell if you owe the CRA money until you do your taxes, and if you do end up owing, there are substantial penalties for filing late. In general, I'd strongly advise filing your tax return in almost all circumstances. Having 401k or HSA is not income and doesn't trigger filing requirements. Withdrawing from 401k or HSA does. Also, in some States, HSA gains are taxed as investment income, so if you have gains in an HSA and you're a resident of such a State - you'll need to file a State tax return and pay taxes on the gains. Answering for just the US part, yes, you should be able to do this and it's a good strategy. The only additional gotcha I can think of is that if you've made after-tax contributions to your traditional IRA, you need to prorate the conversion, you can't just convert all the pre-tax or all the after-tax. I'm not familiar with Oregon personal income tax so there may be additional gotchas there. A couple things. First of all, most people's MAIN source of income is from their job, but they have others, such as bank interest, stock dividends, etc. So that income has to be reported with their wage income. The second thing is that most people have deductions NOT connected with their job. These deductions reduce income (and generate refunds). So it's in their interest to file. Yes, you do. Depending on your country's laws and regulations, since you're not an employee but a self employed, you're likely to be required to file some kind of a tax return with your country's tax authority, and pay the income taxes on the money you earn. You'll have to tell us more about the situation, at least let us know what country you're in, for more information. Yes, you need to include income from your freelance work on your tax return.  In the eyes of the IRS, this is self-employment income from your sole-proprietorship business. The reason you don't see it mentioned in the 1040EZ instructions is that you can't use the 1040EZ form if you have self-employment income.  You'll need to use the full 1040 form.  Your business income and expenses will be reported on a Schedule C or Schedule C-EZ, and the result will end up on Line 12 of the 1040.  Take a look at the requirements at the top of the C-EZ form; you probably meet them and can use it instead of the more complicated C form. If you have any deductible business expenses related to your freelance business, this would be done on Schedule C or C-EZ. If your freelance income was more than $400, you'll also need to pay self-employment tax.  To do this, you file Schedule SE, and the tax from that schedule lands on form 1040 Line 57. "In the U.S., Form 1040 is known as the tax return.  This is the form that is filed annually to calculate your tax due for the year, and you either claim a refund if you have overpaid your taxes or send in a payment if you have underpaid.  The form is generally due on April 15 each year, but this year the due date is April 18, 2016. When it comes to filing your taxes, there are two questions you need to ask yourself: ""Am I required to file?"" and ""Should I file?"" Am I required to file? The 1040 instructions has a section called ""Do I have to file?"" with several charts that determine if you are legally required to file.  It depends on your status and your gross income.  If you are single, under 65, and not a dependent on someone else's return, you are not required to file if your 2015 income was less than $10,300.  If you will be claimed as a dependent on someone else's return, however, you must file if your earned income (from work) was over $6300, or your unearned income (from investments) was over $1050, or your gross (total) income was more than the larger of either $1050 or your earned income + $350.  See the instructions for more details. Should I file? Even if you find that you are not required to file, it may be beneficial to you to file anyway.  There are two main reasons you might do this: If you have had income where tax has been taken out, you may have overpaid the tax.  Filing the tax return will allow you to get a refund of the amount that you overpaid. As a student, you may be eligible for student tax credits that can get you a refund even if you did not pay any tax during the year. How to file For low income tax payers, the IRS has a program called Free File that provides free filing software options." 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. From the Massachusetts Department of Revenue:   1st - Massachusetts Source Income That is Excluded   Massachusetts gross income excludes certain items of income derived from sources within Massachusetts: non-business related interest, dividends and gains from the sale or exchange of intangibles, and qualified pension income. 2nd - Massachusetts Source Income That is Included:   Massachusetts gross income includes items of income derived from sources within Massachusetts. This includes income: 3rd - Trade or business, Including Employment Carried on in Massachusetts:   A nonresident has a trade or business, including any employment carried on in Massachusetts if: A nonresident generally is not engaged in a trade or business, including any employment carried on in Massachusetts if the nonresident's presence for business in Massachusetts is casual, isolated and inconsequential. A nonresident's presence for business in Massachusetts will ordinarily be considered casual, isolated and inconsequential if it meets the requirements of the Ancillary Activity Test (AAT) and Examples. When nonresidents earn or derive income from sources both within Massachusetts and elsewhere, and no exact determination can be made of the amount of Massachusetts source income, an apportionment of income must be made to determine that amount considered Massachusetts gross income. 4th - Apportionment of Income:   Apportionment Methods:   The three most common apportionment methods used to determine Massachusetts source income are as follows:   Gross income is multiplied by a:   So if you go to Massachusetts to work, you have to pay the tax.  If you collect a share of the profit or revenue from Massachusetts, you have to pay tax on that.  If you work from Oregon and are paid for that work, then you don't pay Massachusetts tax on that.  If anything, your company might have to pay Oregon taxes on revenue you generate (you are their agent or employee in Oregon).   Does the answer change depending on whether the income is reported at 1099 or W-2? This shouldn't matter legally.  It's possible that it would be easier to see that the work was done in Oregon in one or the other.  I.e. it doesn't make any legal difference but may make a practical difference.   All this assumes that you are purely an employee or contractor and not an owner.  If you are an owner, you have to pay taxes on any income from your Massachusetts business.  Note that this applies to things like copyrights and real estate as well as the business.   This also assumes that you are doing your work in Oregon.  If you live in Oregon and travel to Massachusetts to work, you pay taxes on your Massachusetts income in Massachusetts. You're doing business in the US and derive income from the US, so I'd say that yes, you should file a non-resident tax return in the US. And in Connecticut, as well, since that's where you're conducting business (via your domestic LLC registered there). Since you paid more than $600 to your contractor, you're probably also supposed to send a 1099 to him on that account on behalf of your LLC (which is you, essentially, if you're the only member). In the USA, you probably owe Self Employment Tax. The cutoff for tax on this is 400$. You will need to file a tax return and cover the medicaid expenses as if you were both the employer and employee.  In addition, if he earns income from self-employment, he may owe Self-Employment Tax, which means paying both the employee’s and employer's share of Social Security and Medicaid taxes. The trigger for Self Employment Tax has been $400 since 1990, but the IRS may change that in the future. Also see the IRS website.  So yes, you need to file your taxes. How much you will pay is determined by exactly how much your income is.  If you don't file, you probably won't be audited, however you are breaking the law and should be aware of the consequences. "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."