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So Roth contributions in after-tax, and any withdrawal of contributions come out without penalty- and contributions comeout first, before earnings. Let's say someone has $20,000 in a roth brokerage. If they are investing in income producing securities like selling options, junk bonds, investment trusts, etc... could they hypothetically contribute $5000 to their Roth every year, and then withdraw $5000 every year as well? Of course they would only be taking out contributions.

Now this isn't the prosperous retirement plan, it's the "avoid taxes now" plan... but is this a legitimate strategy, and is it against IRS regulations?
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