Hi, @bencundiff.
This is not a dumb question at all. Capital losses are not at all straightforward.
First, we need to make sure you are aware that you can only use a maximum of $3,000 to offset ordinary income each year. As an example, say you have:
Capital Losses: $50,000
Capital Gains: 10,000
Net Loss: 40,000
You would only be able to take a $3,000 loss, and the remaining $37,000 would carry over to the next year, where it can be used to offset gains, plus another $3,000.
It's not the payment of monthly dividends that will complicate your taxes, but the re-investment (through DRIP or not). If you sell all of your stock, some of your gain or loss will be short-term, as you will have held the last twelve months' of DRIP shares less than one year. Also, you will have a different purchase price (basis) for each of those buys.
As a reminder, only long-term capital gains receive the lower capital gains rates; short-term gains are taxed at ordinary income rates up to 37%.
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