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1.After the dividend is reinvested (I know I'd have sold before getting dividends), we'll have the total of 92.375 or something shares (now we've got 90.23sh.+2.2sh. estimate with Div. reinvestment). Since fractional shares cannot be sold, we'd sell 92 shares. Question: Can I still use average cost when preparing Schedule D or will I have to use individual shares listing about 30 lines of various fractional shares until I come to the total of 92?

You should be able to make this cleaner i.e. talk to your broker about selling ALL 92.375 shares. (I have a Buy & Hold account that allows purchase of partial shares and DRIP. While I cannot put in order to sell partial shares i.e I couldn't place an order to sell 25.5 shares, there is an option to "sell all shares" ). The clearing method might differ from broker to broker, but the mechanism has to exist

If you are able to accomplish the above, then I believe you can simplify the matter by separating your purchases into long-term (shares held more than a year) and short term (shares held less than a year)

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