US Expatriate, do I have to file for an extension, or do I automatically get it, as in without doing anything?
"The 2 months extension is automatic, you just need to tell them that you're using it by attaching a statement to the return, as Pete Becker mentioned in the comments. From the IRS pub 54: How to get the extension.   To use this automatic 2-month extension, you must attach a statement to your return explaining which of the two situations listed earlier qualified you for the extension.  The ""regular"" 6 months extension though is granted automatically, upon request, so if you cannot make it by June deadline you should file the form 4868 to request a further extension. Automatic 6-month extension.   If you are not able to file your return by the due date, you generally can get an automatic 6-month extension of time to file (but not of time to pay). To get this automatic extension, you must file a paper Form 4868 or use IRS e-file (electronic filing). For more information about filing electronically, see E-file options , later.  Keep in mind that the due date is still April 15th (18th this year), so the 6-month extension pushes it back to October. Previous 2-month extension.   If you cannot file your return within the automatic 2-month extension period, you generally can get an additional 4 months to file your return, for a total of 6 months. The 2-month period and the 6-month period start at the same time. You have to request the additional 4 months by the new due date allowed by the 2-month extension.  You can ask an additional 2 months extension (this is no longer automatic) to push it further to December. See the publication. These are extension to file, not to pay. With the form 4868 you're also expected to submit a payment that will cover your tax liability (at least in the ballpark). The interest is pretty low (less than 1% right now), but there's also a penalty which may be pretty substantial if you don't pay enough by the due date. See the IRS tax topic 301. There are ""safe harbor"" rules to avoid the penalty."
1) Document that you held the bitcoins for more than one year. This should not be particularly difficult. Since you haven't moved the bitcoins, you hold the key to an address that has held them for more than one year. While this isn't absolute proof, it should be sufficient. 2) Since you can't document how you bought them easily, you can just assume a tax basis of zero. This will mean you will pay microscopically more in taxes, but don't worry about it. 3) Sign up with an exchange that can handle your sales. Coinbase will work if you want to sell it slowly. Gemini will work if you want to sell more quickly. 4) Get a decent, secure bitcoin wallet. Transfer the bitcoins to the exchange only as you're selling them. Make you first sale fairly small just in case something goes wrong. 5) Keep meticulous notes about each sale -- the date of the sale, the number of bitcoins you sold, and the number of dollars you got. 6) Make sure to keep enough money for taxes. In Michigan, 24.3% would be the highest possible tax rate you might have to pay if you sold a lot or had high income otherwise. 7) Either get a professional to file your taxes for you or learn how to correctly report long-term capital gains. You must report each individual sale. You may get audited or investigated, but there's nothing to find. The bitcoins have been in stasis for a long time, and it's completely plausible that you bought them and held them. If you can find any proof you bought them (such as a transfer to an exchange) that would be great, but it's not essential. Many people have this same story and unless you're connected to something illegal, you probably don't have anything to worry about. Congratulations! So thats my question, what steps do I need to take to declare this money and obtain it without getting arrested / investigated? There's nothing special you need to do other than keep very good documentation. When you file your taxes, you will need to declare each sale. (This answer assumes that you didn't have a lot of income last year and significantly less income this year. If that's the case, you may have to pay estimated taxes to avoid a penalty. But that penalty is very small and will be calculated by the IRS for you automatically. So I wouldn't worry about it.) You may wish to read up on gift taxes to understand how they work. You won't owe any, but you may need to file paperwork with the IRS if you give large gifts (over $14,000) to people and you will use up some of your lifetime exemption. Keep records of any gifts you give. You understand that inhalation/smoking isn't the only route of administration for THC (active drug in pot), right? Pseudo-Pharmaceutical grade cannabinoid extractions are already used as medication for those with excruciating GI issues, glaucoma and seizure disorders.   The only reason smoking the buds is the preferred method of consumption is because it's the base form and easy to come by. It's (typically) too expensive for one to refine the drug themselves, too risky legally or too dangerous without a controlled laboratory setting. Due to the length of its illegality, extensive research is prohibited to even determine what benefits it could even have in these forms.   You have no idea what therapeutic dosing or high grade cannabinoids could even do because no one is allowed to do it. Especially not doctors trying to keep their medical licenses.   Also I disagree that the benefits of opioids outweigh the side effects. That's why we're having the opioid crisis in the first place. Highly addictive and can lead to overdose. While there is no single case of THC overdose.   (Forensic drug chemist here, not talking out my ass) Here would be the big two you don't mention: Time - How much of your own time are you prepared to commit to this? Are you going to find tenants, handle calls if something breaks down, and other possible miscellaneous issues that may arise with the property? Are you prepared to spend money on possible renovations and other maintenance on the property that may occur from time to time? Financial costs - You don't mention anything about insurance or taxes, as in property taxes since most municipalities need funds that would come from the owner of the home, that would be a couple of other costs to note in having real estate holdings as if something big happens are you expecting a government bailout automatically? If you chose to use a property management company for dealing with most issues then be aware of how much cash flow could be impacted here. Are you prepared to have an account to properly do the books for your company that will hold the property or would you be doing this as an individual without any corporate structure? Do you have lease agreements printed up or would you need someone to provide these for you? Well, if you only own the option, you are only limited to loosing the premium. With futures, at least with the brokers I talked to, most of the time you need to sign a margin contract just to trade futures. I don't want to go into debt, and I don't think I would do too well to be fairly honest. I am a college student, and want to limit my risk, and so just trading the option would help me get access to the commodity markets without having to get margin like many brokers want me to do. I am not trying to do any hedging or anything (which I am aware you can do). All I want to do is do an inflation trade, and I believe commodities are the best way. To me honest, if I had my way I would just buy and hold, and that is the strategy I want to emulate closest, even though I know I can't hold it forever. Basically, I want to avoid debt, but still trade commodities. "What do you mean by ""Canadian income""? Was it income paid to you as wages for the job you did in the US? Or rental/interest income in Canada? If the former - then it doesn't go to NEC, it goes to the main part of the return. If the latter - it doesn't appear on your NR return at all. Yes, it is to validate your residency status. It has no other effect on your taxes." The IRS allows filers to attach a statement explaining the reason for late filing.  I have had clients do this in the past, and there has never been an issue (not that that guarantees anything, but is still good to know). Generally, the IRS is much more lenient when a taxpayer voluntarily complies with a filing requirement, even if it's late, than if they figure it out themselves and send a notice. You are going to have to talk to your benefits office to understand all the deadlines and rules for their program. While the IRS does enforce the law, there are enough local variations in the rules to make it quite complex.   The first thing you  need to know is the source of the funds: the employer or the employee. Then you need to know the deadline for applying for the program, how you specify the monthly expenses in advance, and when the funds expire.  The way you pay for commuting and parking makes a difference: per-ride on the subway, van pool, monthly transit pass; daily parking at a lot, monthly hang tag,  or at meter; These options determine how to expend the funds and how they give you the funds. You can't get money for missed months. So you need to know what you have to do in October to get money for November. Okay so I have just had a phone call with US Ambassy in CZ and they told me that ESTA is only for business trips without earning any money in US ...  So that I will need a US entity (some company/person) to sign some kind of petition for my models before they travel to US and vouch for them ...  Is that correct? Anybody knows how much that costs?  Also they gave me this website: https://www.uscis.gov/  And said it has to be all arranged in US, that they can't do anything on their CZ part.