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Welcome to the Fool. You wrote:

If I were to lose my job and struggle to find another that met my financial needs, how would a sell-off of say $5000.00 of simple stock be taxed?

When you sell a stock held in a regular investment account you have a capital gain or loss, depending on whether you sold for a gain or loss. You track these things by keeping your trade confirmations. When you sell you staple the sale confirmation to the buy confirmation and put it in this year's tax file.

Take a look at the FAQ---------------------------------->
There's a lot of information about these issues there.

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