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"2. Proceeds from Roth IRAs are non-taxable so if I were to hit a few homeruns, I could take the profits without paying taxes on them, but if I did it outside of a Roth structure, I would be hit with a tax."

Careful. Only QUALIFIED distributions are tax free. Before age 59 1/2 only CONTRIBUTIONS are tax and penalty free. Before that age, absent other exceptions such as disability, qualified home purchase, etc., distributions of Roth EARNINGS are not only taxable, but subject to an additional 10% penalty.

See IRS Pub 590 for more information. Here's a link http://www.irs.gov/pub/irs-pdf/p590.pdf

-drip
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