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Are there any benefits to either approach or would I basically be taxed the same irregardless if I were to sell it all or in chunks?

You are taxed the same long-term cap gains rate whether you sell after 1 year or after 10 years. Stock price (as well as tax laws) can change over the years though, affecting how much you might pay in taxes. The real question is whether you want to pay cap gains on all 500 shares in one year, or spread it out over more years. That all depends on your other finances, whether you like the stock and want to keep some shares, etc., etc.

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