Does Robinhood calculate fees and taxes over the total gain/loss or per-transaction?
I don't see a tag for United States, so I'm having to assume this is US taxes.  It doesn't matter what app you use, IRS trades are all calculated the same. First, you have to report each trade on a 8949 and from that the totals go into a schedule D.  Short term trades are stocks that you've kept exactly one year or less, long term trades are for 1 year + 1 day or more.  Trades where you sold a stock for a loss, then bought that stock back again under 30 days don't get to count as a loss.  This only affects realized capital gains and losses, you don't count fees. First, take all of your short term gains then offset them by all of your short term losses.  Do the same for long term gains and losses.  Short and long term gains are taxed at different rates.  You can deduct losses from short term to your long term and vice versa.  Then you can deduct the total losses up to $3000 (household, $1500 married, filing separately) per year on your regular income taxes or other dividend taxes.  If you have over $3000 in losses, then you need to carry that over to subsequent years. Edited per Dave's comments: thanks Dave
Treat each transaction as separate, with its own principal, its own gain, and its own number of days.  Then the total annualized return is just a weighted average of each annualized return, with the weighting related to the number of shares in that transaction. E.g. I buy 1 stock unit for $100.00 and sell it later for $150.00 => income taxes arise. Correct. You pay tax on your gains, i.e.: the different between net proceeds and gross costs (proceeds sans fees, acquisition costs including fees). I buy 1 stock unit for $150.00 and sell it later for $100.00 => no income taxes here. Not correct. The loss is deductible from other capital gains, and if no other capital gains - from your income (up to $3000 a year, until exhausted). Also, there are two different tax rate sets for capital gains: short term (holding up to 1 year) and long term (more than that). Short term capital gains tax matches ordinary income brackets, whereas long term capital gains tax brackets are much lower. "All discount brokers offer a commission structure that is based on the average kind of order that their target audience will make. Different brokers advertise to different target audiences. They could all have a lot lower commissions than they do. The maximum commission price for the order ticket is set at $99 by the industry securities regulators. When discount brokers came along and started offering $2 - $9.99 trades, it was simply because these new companies could be competitive in a place where incumbents were overcharging. The same exists with Robinhood. The market landscape and costs have changed over the last decade with regulation NMS, and other brokerage firms never needed to update drastically because they could continue making a lot on commissions with nobody questioning it. The conclusion being that other brokers can also charge a lot less, despite their other overhead costs. Robinhood, like other brokerage firms (and anyone else trading directly with the exchanges), are paid by the exchanges for adding liquidity. Not only are many trades placed with no commission for the broker, they actually earn money for placing the trade. If Robinhood was doing you any favors, they would be paying you. But nobody questions free commissions so they don't. Robinhood, like other brokerage firms, sells your trading data to the highest bidder. This is called ""payment for order flow"", these subscribers see your order on the internet in route to the exhange, and before your order gets to the exchange, the subscriber sends a different order to the exchange so they either get filled before you do (analogous to front running, but different enough to not be illegal) or they alter the price of the thing you wanted to buy or sell so that you have to get a worse price. These subscribers have faster computers and faster internet access than other market participants, so are able to do this so quickly. They are also burning a lot of venture capital like all startups. You shouldn't place too much faith in the idea they are making [enough] money. They also have plans to earn interest off of balances in a variety of ways and offer more options at a price (like margin accounts)." In no ways. Both will be reported to the members on their K1 in the respective categories (or if it is a single member LLC - directly to the individual tax return). The capital gains will flow to your personal Schedule D, and the business loss to your personal Schedule C. On your individual tax return you can deduct up to 3K of capital losses from any other income. Business loss is included in the income if it is active business, for passive businesses (like rental) there are limitations. Your three options are: Options 2 and 3 are obviously identical (other than transaction costs), so if you want to keep the stock, go for option 1, otherwise, go for option 3 since you have the same effect as option 2 with no transaction costs.  The loss will likely also offset some of the other short term gains you mentioned. 12b1's have fallen out of favor in recent years, and are typically capped at about 0.25%. they are also usually waived and factored into the fund OER these days, too, though it depends on who your broker is.  any revenue sharing shouldn't increase your fees. in my experience, there is more incentivizing for cross selling rather than revenue sharing, but in any case those would be fractions of your revenue allocated to different parties, and not additional fees. does it still count as a capital gain or loss? Yes. Is it essentially treated like you sold the stock at the price of the buy-out?  Yes. Do you still get a 1099-B from your broker? Yes. The way the wash sale works is your loss is added to your cost basis of the buy.  So suppose your original cost basis is $10,000.  You then sell the stock for $9,000 which accounts for your $1,000 loss.  You then buy the stock again, say for $8,500,  and sell it for $9,000.  Since your loss of $1,000 is added to your cost basis, you actually still have a net loss of $500. You then buy the stock again for say $10,500,  then sell it for $9,500.  Your $500 loss is added to your cost basis,  and you have a net loss of $1,500. Since you never had a net gain, you will not owe any tax for these transactions. The point of a total return index is that it already has accounted for the capital gains + coupon income. If you want to calculate it yourself you'll have to find the on-the-run 10y bond for each distinct period then string them together to calc your total return. Check XLTP if they have anything "Free, huh? From their Commission and Fee Schedule:  So if you literally bought two shares, then the SEC added one penny in fees and FINRA added one penny as a ""Trading Activity Fee"" Note that there are several other fees on their schedule that may not apply to you. If you had bought 100 shares instead, your total fees would have still been only 2 cents, but you would have lost $4 on the trade.  So the fees are minuscule when you start doing larger orders.   However, That should not discourage you from experimenting and learning.  I'd rather pay 2 cents in fees on a 4 cent loss than 2 cents in fees on a $400 loss.  Just chalk it up to the cost of experience." I wrote a detailed article on Tax Loss Harvesting to show the impact on returns.  For my example, I showed a person in the 15% bracket. In years with no loss, they trade to capture gains at 0% long term rate, thus bumping their basis up. In years with losses, they tax harvest for a 15% effective 'rebate' on that loss.  I showed how for the lost decade 2000-2009, a buy and hold would have returned -1% CAGR, but the tax loss harvester would have gained 1% (just 1% for the decade, not CAGR), ending the decade with no loss.  As one's portfolio grows, the math changes. You can only take $3000 capital loss against ordinary income, and my example relies on the difference between taking a gain for free but using a loss to offset income. Note, the higher earner would take gains at 15%, but losses at 25%, but only for the relatively small portfolio. The benefit for them is to use loss harvesting to offset gains, less so for ordinary income.  As the other answer state, Wealthfront can aid you to do this with no math on your part. I think the answer you are looking for is:  You are not taxed on the original basis (purchase cost) of your investment.  If you pay $30 a share, and sell at $35, the $5 per share gain is taxable at time of sale.  But the $30 basis cost doesn't enter into tax calculations at all.  (So it's important to keep good records on your investments and how much you paid for them at purchase.) "robinhood is a member of finra, just like any other broker.  as such, they can't legally ""lose"" your assets. even if they file bankruptcy, you will get your money back. obviously, any broker can steal your assets, but i doubt robinhood is any more likely to steal from you, even if you are rich. here is a quote from an article on thestreet.com: So, despite the name, the Robinhood philosophy isn't about stealing   from rich, but rather taking perks often reserved for top-tier   investors and giving them to the everyman trader" When you sell a stock that you own, you realize gains, or losses. Short-term gains, realized within a year of buying and selling an asset, are taxed at your maximum (or marginal) tax rate. Long term-gains, realized after a year, are taxed at a lower, preferential rate. The first thing to consider is losses. Losses can be cancelled against gains, reducing your tax liability. Losses can also be carried over to the next tax year and be redeemed against those gains. When you own a bunch of the same type of stock, bought at different times and prices, you can choose which shares to sell. This allows you to decide whether you realize short- or long-term gains (or losses). This is known as lot matching (or order matching). You want to sell the shares that lost value before selling the ones that gained value. Booking losses reduces your taxes; booking gains increases them. If faced with a choice between booking short term and long term losses, I'd go with the former. Since net short-term gains are taxed at a higher rate, I'd want to minimize the short-term tax liability before moving on to long-term tax liability. If my remaining shares had gains, I'd sell the ones purchased earliest since long-term gains are taxed at a lower rate, and delaying the booking of gains converts short-term gains into long-term ones. If there's a formula for this, I'd say it's  (profit - loss) x (tax bracket) = tax paid Would it be worth legitimizing his business or is it too late at this point? To be blunt, you're asking if we recommend that he stop breaking the law. The answer is obviously yes, he should be declaring his income. And it would probably benefit him to get on the same page as his employer (or client) so they can both start obeying the law together. Once he's filed a tax return for 2016 that would certainly help his cause as far as a lender is concerned, and  as soon as he can provide some recent pay stubs (or paid invoices) he should be ready to move forward on the mortgage based on that additional income.