Can you step up your cost basis indefinitely via the 0% capital gains rate?
"Your real question, ""why is this not discussed more?"" is intriguing. I think the media are doing a better job bringing these things into the topics they like to ponder, just not enough, yet.  You actually produced the answer to How are long-term capital gains taxed if the gain pushes income into a new tax bracket? so you understand how it works.  I am a fan of bracket topping. e.g. A young couple should try to top off their 15% bracket by staying with Roth but then using pretax IRA/401(k) to not creep into 25% bracket.  For this discussion, 2013 numbers, a blank return (i.e. no schedule A, no other income) shows a couple with a gross $92,500 being at the 15%/25% line. It happens that $20K is exactly the sum of their standard deduction, and 2 exemptions.  The last clean Distribution of Income Data is from 2006, but since wages haven't exploded and inflation has been low, it's fair to say that from the $92,000 representing the top 20% of earners, it won't have many more than top 25% today. So, yes, this is a great opportunity for most people.  Any married couple with under that $92,500 figure can use this strategy to exploit your observation, and step up their basis each year. To littleadv objection - I imagine an older couple grossing $75K, by selling stock with $10K in LT gains just getting rid of the potential 15% bill at retirement. No trading cost if a mutual fund, just $20 or so if stocks.  The more important point, not yet mentioned - even in a low cost 401(k), a lifetime of savings results in all gains being turned in ordinary income. And the case is strong for 'deposit to the match but no no more' as this strategy would let 2/3 of us pay zero on those gains.  (To try to address the rest of your questions a bit - the strategy applies to a small sliver of people. 25% have income too high, the bottom 50% or so, have virtually no savings. Much of the 25% that remain have savings in tax sheltered accounts. With the 2013 401(k) limit of $17,500, a 40 year old couple can save $35,000. This easily suck in most of one's long term retirement savings. We can discuss demographics all day, but I think this addresses your question.) If you add any comments, I'll probably address them via edits, avoiding a long dialog below." As JoeTaxpayer illustrated, yes you can.  However, one thing to remember is that unless you live in a state with no state income tax, there may be state tax to pay on those gains.  Even so, it's likely a good idea if you expect either your income (or the federal capital gains tax rate) to rise in the future.
I have read in many personal finance books that stocks are a great investment for the long term, because on average they go up 5-7% every year. This has been true for the last 100 years for the S&P500 index, but is there reason to believe this trend will continue indefinitely into the future? It has also been wrong for 20+ year time periods during those last 100 years. It's an average, and you can live your whole career at a loss. There are many things to support the retention of the average, over the next 100 years. I think the quip is out of scope of your actual investment philosophy. But basically there are many ways to lower your cost basis, by reinvesting dividends, selling options, or contributing to your position at any price from a portion of your income, and by inflation, and by the growth of the world economy. With a low enough cost basis then a smaller percentage gain in the index gives you a magnified profit. "You can certainly try to do this, but it's risky and very expensive. Consider a simplified example. You buy 1000 shares of ABC at $1.00 each, with the intention of selling them all when the price reaches $1.01. Rinse and repeat, right? You might think the example above will net you a tidy $10 profit. But you have to factor in trade commissions. Most brokerages are going to charge you per trade. Fidelity for example, want $4.95 per trade; that's for both the buying and the selling. So your 1000 shares actually cost you $1004.95, and then when you sell them for $1.01 each, they take their $4.95 fee again, leaving you with a measly $1.10 in profit. Meanwhile, your entire $1000 stake was at risk of never making ANY profit - you may have been unlucky enough to buy at the stock's peak price before a slow (or even fast) decline towards eventual bankruptcy.  The other problem with this is that you need a stock that is both stable and volatile at the same time. You need the volatility to ensure the price keeps swinging between your buy and sell thresholds, over and over again. You need stability to ensure it doesn't move well away from those thresholds altogether. If it doesn't have this weird stable-volatility thing, then you are shooting yourself in the foot by not holding the stock for longer: why sell for $1.01 if it goes up to $1.10 ten minutes later? Why buy for $1.00 when it keeps dropping to $0.95 ten minutes later? Your strategy means you are always taking the smallest possible profit, for the same amount of risk. Another method might be to only trade each stock once, and hope that you never pick a loser. Perhaps look for something that has been steadily climbing in price, buy, make your tiny profit, then move on to the next company. However you still have the risk of buying something at it's peak price and being in for an awfully long wait before you can cash out (if ever). And if all that wasn't enough to put you off, brokerages have special rules for ""frequent traders"" that just make it all the more complicated. Not worth the hassle IMO." For the record, now that 2011 is here we know that the capital gains tax rate didn't change. Congress extended it for two more years. This shows the uncertainty in trying to maximize earnings based on future changes to the tax code. Yes, the net effect is zero. If you own zero shares by Nov 30, for example, and don't buy any more shares by 12/31, the year is done, and nothing left to account for. "The tax comes when you close the position. If the option expires worthless it's as if you bought it back for $0. There's a short-term capital gain for the difference between your short-sale price and your buyback price on the option. I believe the capital gain is always short-term because short sales are treated as short-term even if you hold them open more than one year. If the option is exercised (calling away your stock) then you add the premium to your sale price on the stock and then compute the capital gain. So in this case you can end up treating the premium as a long-term capital gain. See IRS pub 550 http://www.irs.gov/publications/p550/ch04.html#en_US_2010_publink100010619 Search for ""Writers of puts and calls""" Interesting.  How would they account for it? Monthly? And if so do they modify the cost basis for each lot for the month and then restate?   It's hard to imagine they do that.   I have a million questions regarding this topic do you know where in the regs it is covered? The fundamental issue with leverage (of any sort, really) is that the amplified downsides are extremely likely to more than cancel out amplified equivalent upsides. Example without using a major swing: 2x leverage on a 5% decline (so a 10% decline).  The 5% decline needs a 5.26% increase to get back level.  However, the 2x leverage needs an 5.55% increase to get back.  So a cycle for the unleveraged returns of -5%, +5.4% would see the unleveraged asset go up by a net +0.13% but 2x leverage would leave you at -0.28%.  Conversely, imagine 0.5x leverage (it's easy to do that: 50% cash allocation): after an underlying -5%, the 0.5x leverage needs only +5.13% to reach par.  This is basically the argument for low volatility funds. Of course, if you can leverage an asset that doesn't go down, then the leverage is great.  And for an asset with an overall positive compound return, a little leverage is probably not going to hurt, simply because there are likely to be enough upsides to cancel out downsides. "You uncle is liable to pay ""Capital-Gains"" tax. Essentially the sale price less of cost would be treated as gains. The gains are taxed at 10% without indexation and 20% with Indexation.  The capital gains tax can be avoided if your uncle invests the gains into specified ""Infrastructure bonds"" or buys another property within a period of 3 years. The funds need to be kept in a separate ""Capital Gains"" account and not a regular savings account till you buy another property within 3 years." You may be able to choose.  As a small business, you can expense certain depreciable assets (section 179).  But by choosing to depreciate the asset, you are also increasing the cost-basis of the property.  Are you planning to sell the property in the next couple of years?  Do you need a higher basis? Section 179 - Election to expense certain depreciable business assets "I think so.  I am doing this with our furniture.  It doesn't cost me any more money to pay right now than it will to pay over the course of 3 years, and I can earn interest on the money I didn't spend. But know this: they aren't offering 0%, they are deferring interest for 3 years.  If you pay it off before then great, if you don't you will owe all the accumulated interest. The key with these is that you always pay it, and on time.  Miss a payment and you get hosed.  If you don't pay on time you will owe the interest that is being deferred.  They will also be financing this through a third party (like a major bank) and that company is now ""doing business with you"" which means in the US they can call you and solicit new services.  I am willing to deal with those trade offs though, plus, as you say, you can always pay it off. WHY THEY DO IT (what is in it for them...) A friend of mine works for a major bank that often finances these deals here is how they work. Basically, banks do this to generate leads for their divisions that do cold calls.  If you are a high credit, high income customer you go to a classic bank and request cash, if you are building credit or have bad credit, you go to a ""financial services"" branch.  If you tend to finance things like cars and furniture, you get more cold calls." Yes, just set aside the amount of money. If you buy a cfd long in a stock for a 1000$, set aside 1000$. If you buy a cfd short, set aside the same amount and include a stoploss at the value at which the money is depleted. In this case however, you can stil lose more, because of opening gaps. By doing this, you replicate the stock return, apart from the charged interest rate. Disclaimer: I’m not an expert.  This is my basic understanding, which I’m sure someone will be glad to tell is horribly wrong...  You need an LLC.  Many people in my area create an LLC management company, then create individual LLCs for each investment property.  Laws vary by state.  YMMV  Then you start researching properties.  Commercial loans typically require a higher equity position than home ownership.   Assume minimum 30%.  For ease of this conversation let’s say you’re making the horribly poor decision to put that towards a single property.   You’d be looking for a property in the 175-200k value range, because you’ll need to account for settlement expenses (attorney, broker, consultants) and a cash reserve.  You’d be also be looking for what the average cap rate is for your market.  In simplistic terms cap rate is the expected rate of return after expenses.  So if the average market cap rate in that region for comparable properties is 5%, you can expect around 5% return on your investment, after you pay fees, maintenance, taxes, insurance, interest, etc.  Buy a property and hold that property for a few years, making money every year, and claiming deductions on your earnings for something called depreciation.  Fast forward 5 years and you’re ready to sell, the value of your property went up because you made improvements along the way, brought in some better tenants who are paying higher rents, and now you can offer a better cap rate than your competitors.  You sell in the blink of an eye, and double your investment.  Say you have $500k now sitting in the bank in you LLC’s name, in cash.  You can either choose to cash out 100% and pay capital gains tax on your earnings above your basis (at 15% I think?)... OR you can quickly find a new property with that $500k, purchase it, and file a 1031, which says you don’t have to pay ANY capital gains on those earnings.  You just increased income significantly without ever paying taxes on the underlying increase in value of your assets.  Rinse and repeat for 25 years, develop a portfolio of properties, create a management company so you can stop paying others a percentage of your earnings, and you too can have the problem of too much money.  I welcome anyone with actual knowledge of the topic to please expound on, or correct me. Expenses matter. At the back end, retirement, the most often quoted withdrawal rate is 4%. How would it feel to be paying 1/4 of each years' income to fees, separate from the taxes due, separate from whether the market is up or down? Kudos to you for learning this lesson so early.  Your plan is great, and while I often say 'don't let the tax tail wag the investing dog' being mindful of the tax hit in any planned transaction is worthwhile.  Selling and moving enough funds to stay at 0% is great, a no-brainer, as they say. Selling more depends on the exact numbers involved. Do a fake return, and see how an extra $1000/$2000 etc, worth of fund sale impacts the taxes. It will depend on how much gain there is for each $XXX of fund. Say you are up 25%, So $1000 has $200 of gain. 15% of $200 is $30. A 1%/yr fee cost you $10/yr, so it's worth waiting till January to sell the next shares of the fund.  Keep in mind, the 'test' return will still have the 2013 rates and brackets, I suggest this only as an estimating tool. This is one way in which the scheme could work: You put your own property (home, car, piece of land) as a collateral and get a loan from a bank. You can also try to use the purchased property as security, but it may be difficult to get 100% loan-to-value. You use the money to buy a property that you expect will rise in value and/or provide rent income that is larger than the mortgage payment. Doing some renovations can help the value rise. You sell the property, pay back the loan and get the profits. If you are fast, you might be able to do this even before the first mortgage payment is due. So yeah, $0 of your own cash invested. But if the property doesn't rise in value, you may end up losing the collateral. Generally not, however some brokers may allow it. My previous CFD Broker - CMC Markets, used to allow you to adjust the leverage from the maximum allowed for that stock (say 5%) to 100% of your own money before you place a trade. So obviously if you set it at 100% you pay no interest on holding open long positions overnight. If you can't find a broker that allows this (as I don't think there would be too many around), you can always trade within your account size. For example, if you have an account size of $20,000 then you only take out trades that have a face value up to the $20,000. When you become more experienced and confident you can increase this to 2 or 3 time your account size. Maybe, if you are just starting out, you should first open a virtual account to test your strategies out and get used to using leverage. You should put together a trading plan with position sizing and risk management before starting real trading, and you can test these in your virtual trading before putting real money on the table. Also, if you want to avoid leverage when first starting out, you could always start trading the underlying without any leverage, but you should still have a trading plan in place first.