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No. of Recommendations: 2
How many dividend-paying ideas are you talking about?

If you are talking about less-than-10 names, your fears about it being complicated are overblown.
Three tools that can help

1. Start a spreadsheet.
One can make it fancy or complicated if one wants. I had eight columns to start but six
columns is all one really needs.
Purchase date, # of shares purchased, Cost, Sales date, # of shares sold, Sales. The "stocks"
that caused me to choose the spreadsheet solution were Canadian Royalty trusts (Canroys), many
of which paid their distributions on a monthly basis. One doesn't even have to update the
spreadsheet on a monthly basis. Even once every 3-6 months would work.

2. Brokerage statements
This might vary by brokerage but some brokerages have some really good transaction reporting
documents (either mailed or online). The brokerage where I do most of my DRIP investing has
really good 1099 tax reporting data for customers.

3. Using "various"
One does have to separate long term holdings/transactions from short term holdings/transactions.
But it is possible to consolidate a whole bunch of transactions involving the same
stock ticker into a single line (two lines if the transactions were spread over more
than a year). The spreadsheet mentioned in #1 is useful here.
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