Hi Wradical,
“with the pay dates and ex-div. dates, and each month I will see if it makes sense to buy additional shares of stocks that will pay dividends next month, to get the dividend on the new shares.”
I don’t do this exercise. To me it just does not matter if I get the “next” dividend or not.
When shares go ex-div, the exchanges adjust all open orders by the amount of the payment.
So, if the price is $20 and the dividend is $0.15, the stock price is changed to $19.85 and later on, you receive the $0.15 in cash.
If having the cash a month later is all that important, just hold back $20 or whatever when you buy stock.
In a taxable account, that $0.15/share dividend will increase your taxable income, even if it is a qualified dividend, while the $20 held back is tax free!
Does that help you?
Gene
All holdings and some statistics on my Fool profile page
http://my.fool.com/profile/gdett2/info.aspx