Quarterly dividends to monthly dividends
Technically you should take the quarterly dividend yield as a fraction, add one, take the cube root, and subtract one (and then multiple by the stock price, if you want a dollar amount per share rather than a rate).  This is to account for the fact that you could have re-invested the monthly dividends and earned dividends on that reinvestment. However, the difference between this and just dividing by three is going to be negligible over the range of dividend rates that are realistically paid out by ordinary stocks.
"Dividends are paid based on who owns the security on a designated day.  If a particular security pays once per year, you hold 364 days and sell on the day before the ""critical"" day, you get no dividend.  This is not special to 401(k) or to DRIP.  It's just how the system works. The ""critical"" day is the day before the posted ex-dividend date for the security. If you own at the end of that day, you get the dividend.  If you sell on that day or before, you do not. Your company changing providers is not in itself relevant.  The important factor is whether you can still hold your same investments in the new plan.  If not, you will not get the dividend on anything that you currently hold but ""sell"" due to the change in providers.  If you can, then you potentially get the dividend so long as there's no glitch in the transition. Incidentally, it works the other way too.  You might end up getting a dividend through the new plan for something that you did not hold the full year." The answer to this question requires looking at the mathematics of the Qualified Dividends and Capital Gains Worksheet (QDCGW). Start with Taxable Income which is the number that appears on Line 43 of Form 1040.  This is after the Adjusted Gross Income has been reduced by the Standard Deduction or Itemized Deductions as the case may be, as well as the exemptions claimed.   Then, subtract off the Qualified Dividends and the Net Long-Term Capital Gains (reduced by Net Short-Term  Capital Losses, if any) to get the non-cap-gains part of the Taxable Income. Assigning somewhat different meanings to the numbers in the OPs' question, let's say that the Taxable Income is $74K of which $10K is Long-Term Capital Gains leaving $64K as the the non-cap-gains taxable income on Line 7 of the QDCGW.   Since $64K is smaller than $72.5K (not $73.8K as stated by the OP) and this is a MFJ return, $72.5K - $64K = $8.5K of the long-term capital gains are taxed at 0%. The balance $1.5K is taxed at 15% giving $225 as the tax due on that part.   The 64K of non-cap-gains taxable income has a tax of $8711 if I am reading the Tax Tables correctly, and so the total tax due is $8711+225 = $8936.  This is as it should be; the non-gains income of $64K was assessed the tax due on it, $8.5K of the cap gains were taxed at 0%, and $1.5K at 15%. There are more complications to be worked out on the QDCGW for high earners who attract the 20% capital gains rate but those are not relevant here. The methodology for divisor changes is based on splits and composition changes. Dividends are ignored by the index. Side note - this is why, in my opinion, that any discussion of the Dow's change over a long term becomes meaningless. Ignoring even a 2% per year dividend has a significant impact over many decades.  The divisor can be found at http://wsj.com/mdc/public/page/2_3022-djiahourly.html "EPS is often earnings/diluted shares. That is counting shares as if all convertible securities (employee stock options for example) were converted. Looking at page 3 of Q4 2015 Reissued Earnings Press Release we find both basic ($1.13) and diluted EPS ($1.11). Dividends are not paid on diluted shares, but only actual shares. If we pull put this chart @ Yahoo finance, and hovering our mouse over the blue diamond with a ""D"", we find that Pfizer paid dividends of $0.28, $0.28, $0.28, $0.30 in 2015. Or $1.14 per share. Very close to the $1.13, non-diluted EPS. A wrinkle is that one can think of the dividend payment as being from last quarter, so the first one in 2015 is from 2014. Leaving us with $0.28, $0.28, $0.30, and unknown. Returning to page three of Q4 2015 Reissued Earnings Press Release, Pfizer last $0.03 per share. So they paid more in dividends that quarter than they made. And from the other view, the $0.30 cents they paid came from the prior quarter, then if they pay Q1 2016 from Q4 2015, then they are paying more in that view also." Your example isn't consistent: Q1 end market value (EMV) is $15,750, then you take out $2,000 and say your Q2 BMV is $11,750?  For the following demo calculations I'll assume you mean your Q2 BMV is $13,750, with quarterly returns as stated: 10%, 5%, 10%.  The Q2 EMV is therefore $15,125. True time-weighted return :- http://en.wikipedia.org/wiki/True_time-weighted_rate_of_return  The following methods have the advantage of not requiring interim valuations. Money-weighted return :- http://en.wikipedia.org/wiki/Rate_of_return#Internal_rate_of_return  Logarithmic return :- http://en.wikipedia.org/wiki/Rate_of_return#Logarithmic_or_continuously_compounded_return  Modified Dietz return :- http://en.wikipedia.org/wiki/Modified_Dietz_method  Backcalculating the final value (v3) using the calculated returns show the advantage of the money-weighted return over the true time-weighted return. This answer contains three assumptions: New Share Price: Old Share Price * 1.0125 Quarterly Dividend: (New Share Price*0.01) * # of Shares in Previous Quarter Number of Shares: Shares from Previous Quarter + Quarterly Dividend/New Share Price For example, starting from right after Quarter One: New share price: $20 * 1.0125 = 20.25  1000 shares @ $20.25 a share yields $20.25 * 0.01 * 1000 = $202.5 dividend New shares: $202.5/20.25 = 10 shares Quarter Two: New share price: $20.503 1010 shares @ 20.503 yields $20.503*0.01*1010 = $207.082 dividend New shares: $207.082/20.503 = 10.1 shares Repeat over many cycles: 8 Quarters (2 years): 1061.52 shares @ $21.548 a share 20 Quarters (5 years): 1196.15 shares @ $25.012 a share 40 Quarters (10 years): 1459.53 shares @ $32.066 a share Graphically this looks like this:  It's late enough someone may want to check my math ;). But I'd also assert that a 5% growth rate and a 4% dividend rate is pretty optimistic. Daily &gt; Weekly &gt; Monthly. This statement says that if you use daily returns you will get more noise than if you used weekly or monthly returns. Much of the research performed uses monthly returns, although weekly returns have been used as well. For HFT you would need to detrend the data in order to spot true turning points. Ignoring the wildly unreasonable goal, I'll answer just the Headline question asked. It's possible to choose dividend paying stocks so that you receive a dividend check each month. Dividends are typically paid quarterly, so 3 stocks chosen by quality first, but also for their dividend date will do this. To get $2000/mo or $24,000/yr would only take an investment of $600,000 in stocks that are yielding a 4% dividend. The dividend quoted on a site like the one you linked to on Yahoo shows what 1 investor owning 1 share received from the company. It is not adjusted at all for taxes. (Actually some dividend quotes are adjusted but not for taxes... see below.)  It is not adjusted because most dividends are taxed as ordinary income. This means different rates for different people, and so for simplicity's sake the quotes just show what an investor would be paid.  You're responsible for calculating and paying your own taxes.  From the IRS website: Ordinary Dividends Ordinary (taxable) dividends are the most common type of distribution from a corporation or a mutual fund. They are paid out of earnings and profits and are ordinary income to you. This means they are not capital gains. You can assume that any dividend you receive on common or preferred stock is an ordinary dividend unless the paying corporation or mutual fund tells you otherwise. Ordinary dividends will be shown in box 1a of the Form 1099-DIV you receive. Now my disclaimer... what you see on a normal stock quote for dividend in Yahoo or Google Finance is adjusted. (Like here for GE.) Many corporations actually pay out quarterly dividends. So the number shown for a dividend will be the most recent quarterly dividend [times] 4 quarters. To find out what you would receive as an actual payment, you would need to divide GE's current $0.76 dividend by 4 quarters... $0.19. So you would receive that amount for each share of stock you owned in GE. "You don't. No one uses vanilla double entry accounting software for ""Held-For-Trading Security"".  Your broker or trading software is responsible for providing month-end statement of changes.  You use ""Mark To Market"" valuation at the end of each month.  For example, if your cash position is -$5000 and stock position is +$10000, all you do is write-up/down the account value to $5000.  There should be no sub-accounts for your ""Investment"" account in GNUCash.  So at the end of the month, there would be the following entries:" "Re. question 2 If I buy 20 shares every year, how do I get proper IRR? ... (I would   have multiple purchase dates) Use the money-weighted return calculation: http://en.wikipedia.org/wiki/Rate_of_return#Internal_rate_of_return  where t is the fraction of the time period and Ct is the cash flow at that time period. For the treatment of dividends, if they are reinvested then there should not be an external cash flow for the dividend.  They are included in the final value and the return is termed ""total return"".  If the dividends are taken in cash, the return based on the final value is ""net return"". The money-weighted return for question 2, with reinvested dividends, can be found by solving for r, the rate for the whole 431 day period, in the NPV summation. Now annualising And in Excel" No, they do not. Stock funds and bonds funds collect income dividends in different   ways. Stock funds collect dividends  (as well as any capital gains   that are realized) from the underlying stocks  and incorporates these   into the funds’ net asset value, or daily share price. That’s why a   stock fund’s share price drops when the fund makes a distribution –   the distribution comes out of the fund’s total net assets. With bond funds, the internal accounting is different:  Dividends   accrue daily, and are then paid out to shareholders every month or   quarter.  Bond funds collect the income from the underlying bonds and   keep it in a separate internal “bucket.”  A bond fund calculates a   daily accrual rate for the shares outstanding, and shareholders only   earn income for the days they actually hold the fund.  For example, if   you buy a bond fund two days before the fund’s month-end distribution,   you would only receive two days’ worth of income that month.  On the   other hand, if you sell a fund part-way through the month, you will   still receive a partial distribution at the end of the month,   pro-rated for the days you actually held the fund. Source  Also via bogleheads: Most Vanguard bond funds accrue interest to the share holders daily.   Here is a typical statement from a prospectus: Each Fund distributes to shareholders virtually all of its net income   (interest less expenses) as well as any net capital gains realized   from the sale of its holdings. The Fund’s income dividends accrue   daily and are distributed monthly. The term accrue used in this sense   means that the income dividends are credited to your account each day,   just like interest in a savings account that accrues daily. Since the   money set aside for your dividends is both an asset of the fund and a   liability, it does not affect the calculated net asset value. When the   fund distributes the income dividends at the end of the month, the net   asset value does not change as both the assets and liabilities   decrease by exactly the same amount. [Note that if you sell all of   your bond fund shares in the middle of the month, you will receive as   proceeds the value of your shares (calculated as number of shares   times net asset value) plus a separate distribution of the accrued   income dividends.] Ok so I used Excel solver for this but it's on the right track.  Latest price = $77.19  Latest div = $1.50  3-yr div growth = 28%  g = ???  rs = 14%  So we'll grow out the dividend 3 years @ 28%, and then capitalize them into perpetuity using a cap rate of [rs - g], and take the NPV using the rs of 14%. We can set it up and then solve g assuming an NPV of the current share price of $77.19.  So it should be:  NPV = $77.19 =   [$1.50 / (1+0.14)^0 ] +  [$1.50 x (1+0.28)^1 / (1+0.14)^1 ] +  ... +  [$1.50 x (1+0.28)^3 / (1+0.14)^3 ] +  [$1.50 x (1+0.28)^3 x (1+g) / (0.14-g) / (1+0.14)^4 ]  Which gives an implied g of a little under 9%. Let me know if this makes sense, and definitely check the work... Why do people talk about stock that pay high dividends?  Traditionally people who buy dividend stocks are looking for income from their investments. Most dividend stock companies pay out dividends every quarter ( every 90 days). If set up properly an investor can receive a dividend check every month, every week or as often as they have enough money to stagger the ex-dates. There is a difference in high $$ amount of the dividend and the yield.  A $1/share dividend payout may sound good up front, but... how much is that stock costing you? If the stock cost you $100/share, then you are getting 1% yield. If the stock cost you $10/share, you are getting 10% yield.  There are a lot of factors that come into play when investing in dividend stocks for cash flow. Keep in mind why are you investing in the first place. Growth or cash flow. Arrange your investing around your major investment goals. Don't chase big dollar dividend checks, do your research and follow a proven investment plan to reach your goals safely. I think your math is fine, and also consider insurance costs and the convenience factor of each scenario. Moving a car frequently to avoid parking tickets will become tedious. I'd rather spend an hour renting a car 20 times in a year rather than have to spend 15 minutes moving a car every three days. And if there's no other easy parking, that 15 minutes can take a lot longer. Plus it'll get dirty sitting there, could get vandalized. Yuck. For only 20 days/year, I don't see how owning a car is worth the hassle. I recommend using a credit card that comes with free car rental insurance.