Owned house for less than 2 years - 1031 exchange?
Yes, your realtor is a moron. (I am a realtor, and sorry you have such a bad one) Every industry has its good and bad. You really should find a new realtor, a good one.  You know the 1031 exchange is for rental property only. And that saving $2000 isn't worth staying in the house to complete the two years required occupancy.
"Disclaimer: I am neither a lawyer nor a tax-expert This page on the HMRC site lists several pages that appear to be relevant, starting with CG78401 - Foreign currency: delayed remittances and on to CG78408 - Foreign currency: example which seems pertinent to your case [paraphrased]: A property bought in 1983 is sold for a [taxable] gain in one tax-year (1986/87) but the proceeds cannot be released/remitted to the UK until later (1991/92), by which time currency fluctuations have created a second [taxable] gain. The size of the first gain (selling the property) is determined by the exchange rate in effect at the time of the sale but because of local restrictions, this can be deferred.  The size of the second gain (currency movement) is determined by the change in exchange-rate between the time of the sale and the time of conversion. In your case, the first ""gain"" was actually a loss, so I believe you should be able to use this to offset any tax due second gain.  This page states that losses can be claimed up to four years after the end of the tax-year in which they were incurred, so you are probably still OK. (The example makes application under TCGA92/S279 to defer the gain made on the original sale [because of the inability to transfer funds], but as I understand it, this is primarily to avoid a tax liability in that year.  Since you made a loss on the sale, there wouldn't have been a tax liability, so there would be no need to defer it)." "You mention ""early exercise"" in your title, but you seem to misunderstand what early exercise really means. Some companies offer stock options that vest over a number of years, but which can be exercised before they are vested. That is early exercise. You have vested stock options, so early exercise is not relevant. (It may or may not be the case that your stock options could have been early exercised before they vested, but regardless, you didn't exercise them, so the point is moot.) As littleadv said, 83(b) election is for restricted stocks, often from exercising unvested stock options. Your options are already vested, so they won't be restricted stock. So 83(b) election is not relevant for you. A taxable event happen when you exercise. The point of the 83(b) election is that exercising unvested stock options is not a taxable event, so 83(b) election allows you to force it to be a taxable event. But for you, with vested stock options, there is no need to do this. You mention that you want it not to be taxable upon exercise. But that's what Incentive Stock Options (ISOs) are for. ISOs were designed for the purpose of not being taxable for regular income tax purposes when you exercise (although it is still taxable upon exercise for AMT purposes), and it is only taxed when you sell. However, you have Non-qualified Stock Options. Were you given the option to get ISOs at the beginning? Why did your company give you NQSOs? I don't know the specifics of your situation, but since you mentioned ""early exercise"" and 83(b) elections, I have a hypothesis as to what might have happened. For people who early-exercise (for plans that allow early-exercise), there is a slight advantage to having NQSOs compared to ISOs. This is because if you early exercise immediately upon grant and do 83(b) election, you pay no taxes upon exercise (because the difference between strike price and FMV is 0), and there are no taxes upon vesting (for regular or AMT), and if you hold it for at least 1 year, upon sale it will be long-term capital gains. On the other hand, for ISOs, it's the same except that for long-term capital gains, you have to hold it 2 years after grant and 1 year after exercise, so the period for long-term capital gains is longer. So companies that allow early exercise will often offer employees either NQSOs or ISOs, where you would choose NQSO if you intend to early-exercise, or ISO otherwise. If (hypothetically) that's what happened, then you chose wrong because you got NQSOs and didn't early exercise." And he has to pay for it every home repair and every month the property sets empty.  His loss each month is not $250, but probably closer to $500.  In generally you need to clear at least $200 ABOVE PTI (principle, taxes and interest) to cover repair and the like to property. From your post, it sounds like your dad was forced into the land-lord business by the recession.  Unless he plans to hold the property until its rental value has increased by $500 a month, he should consider selling it and writing-off the loss.  Losing money bit by bit on a house isn't a tax write-off event.  Selling a property for less than you bought it for generally is. FYI, I got the $500/month loss by assuming that repairs/emptiness/etc will cost you about $200 a month, and added $50 for your dad's time managing the property. "There some specific circumstances when you would have a long-term gain. Option 1:  If you meet all of these conditions: Then you've got a long-term gain on the stock.  The premium on the option gets rolled into the capital gain on the stock and is not taxed separately.  From the IRS: If a call you write is exercised and you sell the underlying stock, increase your amount realized on the sale of the stock by the amount you received for the call when figuring your gain or loss. The gain or loss is long term or short term depending on your holding period of the stock. https://www.irs.gov/publications/p550/ch04.html#en_US_2015_publink100010630 Option 2: If you didn't hold the underlying and the exercise of the call that you wrote resulted in a short position, you might also be able to get to a long-term gain by buying the underlying while keeping your short position open and then ""crossing"" them to close both positions after one year. (In other words, don't ""buy to cover"" just ""buy"" so that your account shows both a long and a short position in the same security.  Your broker probably allows this, but if not you, could buy in a different account than the one with the short position.)  That would get you to this rule: As a general rule, you determine whether you have short-term or long-term capital gain or loss on a short sale by the amount of time you actually hold the property eventually delivered to the lender to close the short sale. https://www.irs.gov/publications/p550/ch04.html#en_US_2015_publink100010586 Option 1 is probably reasonably common.  Option 2, I would guess, is uncommon and likely not worthwhile. I do not think that the wash sale rules can help string along options from expiration to expiration though.  Option 1 has some elements of what you wrote in italics (I find that paragraph a bit confusing), but the wash sale does not help you out." "Let's illustrate how typical mortgage and its insurance works, from the very beginning. few years pass You're at the last point now. The whole point of the insurance was to preserve value of bank's collateral, at least from its point of view. By making a claim you have testified that a damage has occurred and some value of the property was lost. It's only reasonable for the bank that it wants the value of the asset to be restored to the value of the loan. Or the other way around. Bank doesn't really care if your deck is repaired, it only cares to have right side equal left side in the books. By taking the mortgage you've agreed to preserve the value of the property. There are many ways out of this situation, but pocketing the money isn't one of them.  There is no need to fight the mortgage company, because they're right. Talk with them in good faith and walk through available options. If you feel that you can live with the deck as it is, then paying back part of the loan might be a good idea. You don't ""lose"" the money this way, you're still 2k ahead - just not now, but in 20 years.  Afterthought: it's possible that it would be ""enough"" to re-evaluate the house to ensure it's still worth its original value even with damaged deck (eg due to other improvements you've made over the years or general property prices rising in the area). I put quotes, because you have to count costs of reevaluation which may be too big to make it worth. AND it might turn out it's worth even less, eg if the prices dropped. Or add another collateral, but that means signing another lien which also costs money." This new roof should go on the 2016 LLC business return, but you probably won't be able to expense the entire roof as a repair.  A new roof is most likely a capital improvement, which means that it would need to be depreciated over many years instead of expensed all in 2016.  The depreciation period for a residential rental property is 27.5 years.  Please consider seeking a CPA or Enrolled Agent for the preparation of your LLC business return. See also: IRS Tangible Property Regulations FAQ list When you made the loan to the LLC (by paying the contractor and making a contract with the LLC), did you state an interest rate?  If not, you and your brother should correct the contract so that an interest rate is stated, then follow it.  The LLC needs to pay you interest until the loan is paid off.  You need to report the interest income on your personal return, and the LLC needs to report the interest expense in its business return. I don't see anything in this forum on the leverage aspect, so I'll toss that out for discussion.  Using generic numbers, say you make a $10k down payment on a $100,000 house. The house appreciates 3% per year. First year, it's $103,000. Second year, $106090, third it's 109,272.70. (Assuming straight line appreciation.) End of three years, you've made $9,272.70 on your initial $10,000 investment, assuming you have managed the property well enough to have a neutral or positive cash flow. You can claim depreciation of the property over those rental years, which could help your tax situation.   Of course, if you sell, closing costs will be a big factor. Plus... after three years, the dreaded capital gains tax jumps in as mentioned earlier, unless you do a 1031 exchange to defer it. $100K is not a lot for my $335K house (now appraised at $389K after 2 years...wtf), with Taxes close to $11500 per year. I'm paying 30K per year JUST for the house+escrow. Now factor in utilities, food, cars, insurance, healthcare, etc. If you held the shares directly, the transfer agent, Computershare, should have had you registered and your address from some point on file.  I have some experience with Computershare, it turned out when Qwest restarted dividends and the checks mailed to the childhood home my parents no longer owned, they were able to reissue all to my new address with one telephone call.  I can't tell you what their international transfer policies or fees might be, but if they have your money, at least its found. Transfer Agent Computershare Investor Services serves as the stock transfer agent for Tellabs. If you need to transfer stock, change ownership, report lost or stolen certificates, or change your address, please contact Computershare Investor Services at +1.312.360.5389. "I've found that once people ""fall in love"" with a home or the idea of a home, there's little chance they will chance course.    I'd implore you to do some reading about individuals and families trapped in an underwater mortgage and having lost a job -- now they can't move for work, and they can't refinance or sell.  In short, they are trapped and will be foreclosed upon (or, at best, will short-sell).  If you want to play knife-catcher (e.g., trying to buy an asset while its value is falling) then at least don't go in blind or kid yourself about the risks.  Of course, many folks believe the housing market has bottomed - if that's true then there's no harm in waiting 6 or 12 months and verifying that premise.  At most, you'll lose a couple of points in equity.    On the other hand, you may well discover that all is not well, and suddenly you can ""afford"" even ""more"" house.  It is not hyperbole to say that the housing market in the USA has financially destroyed millions of people -- be careful out there especially as Europe comes unglued." If there are a lot of houses for sale, can you be sure that in a year or two you can sell yours? How long does the average house in that area stay on the market before it is sold? What percentage of houses never get sold?  If it can't be sold due to the crowded market you will be forced to rent the house. The question for you then is how much rental income can you get? Compare the rental income to your monthly cost of owning, and managing the house.  One benefit to buying a house in a market that is easy to rent a house would be if you are forced to move quickly, then you aren't stuck being 3 months into a 12 month lease.  Keep in mind that markets can change rather dramatically in just a few years. Housing costs were flat for much of the 90's, then rocketed up in the first half of the last decade, and after a big drop, they are one a slow climb back up. But the actual path they are on depends on the part of the US you are in.  The rule of thumb in the past was based on the fact that over a few years the price would rise enough overcome the closing costs on the two transactions. Unfortunately the slow growth in the 90's meant that many had to bring checks to closing because the equity gained wasn't enough to overcome the closing costs due to low down payment loans.   The fast growth period meant that people got into exotic loans to maximize the potential income when prices were going up 10-20% a year.  When prices dropped some found that they bought houses they couldn't afford, but couldn't sell to break even on the transaction. They were stuck and had to default on the mortgage.  In fact I have never seen a time frame when the rule of thumb ever applied. "If it was me, I would sell the house and use the proceeds to work on/pay off the second.   You don't speak to your income, but it must be pretty darn healthy to convince someone to lend you ~$809K on two homes.  Given this situation, I am not sure what income I would have to have to feel comfortable.  I am thinking around 500K/year would start to make me feel okay, but I would probably want it higher than that. think I can rent out the 1st house for $1500, and after property management fees, take home about $435 per month. That is not including any additional taxes on that income, or deductions based on repair work, etc. So this is why.  Given that your income is probably pretty high, would something less than $435 really move your net worth needle?  No.  It is worth the reduction in risk to give up that amount of ""passive"" income.  Keeping the home opens you up to all kinds of risk.  Your $435 per month could easily evaporate into something negative given taxes, likely rise in insurance rates and repairs.  You have a great shovel to build wealth there is no reason to assume this kind of exposure.  You will become wealthy if you invest and work to reduce your debt." One piece of information you didn't mention is how much you paid for the original home.  If you hold onto that home for too long you will have to pay capital gains on the difference between sale price and original price. This can be a TON of money, thousands of dollars easily. The rule is: If you lived in a home for 2 out of the past 5 years, you don't have to pay the capital gains tax. So  if you just moved, you have 3 years to sell.  Perhaps as a compromise you can try renting it for 3 years and then selling it a few months before the deadline. Where I am you pay annual taxes on a house, pay state and county transfer taxes when you buy/sell, and then have to pay capital gains the year you sell if it appreciated and you don't meet one of the exemptions. So I think your whole premise may be flawed. When you sell a house around between 7-10% of the sales price will go to various fees. Mostly to the agents, but also to county fees, city fees, deed tax, and possibly covering closing costs for the buyers. So if you sell a $400k house for the same price you buy, just in fees, you're out $40k. Mortgages are structured so that the frontend is very interest heavy, while at the end you're mostly paying towards principal. So for the first two years you will pay down very little of the principal. Figure around $2500 for the mortgage, and without running the numbers I bet you would pay an average for the first two years of around $1800/month in interest. $43,200. Mortgage interest is tax deductible, so you'll get some of that back. That's also $16,800 in equity you'll have on the house, so you'll get that back out when you sell. Rough numbers, I would be you lose around $50k buying the house and selling for the same price two years later. That doesn't take into account having to do any maintenance. And it assumes you can sell quickly when you want to. Renting is not throwing away money. You don't lose any money. You get a place to live in exchange. You don't build equity, sure, but you don't need to worry about maintenance and other related issues. When you're looking to be somewhere short term renting is generally the best idea.