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1. The 5 year rule begins on Jan 1 of year for which the first Roth contribution is made. This can be a direct contribution or conversion contribution. So for example, if your first Roth contribution is Feb 2, 2021 but is designated for 2020, the start date is Jan 1, 2020 and the 5 year holding period will be met Jan 1, 2025.

2. An IRA, Traditional or Roth, is NOT an investment, it's an account with special tax favored rules. What you invested in is irrelevant. If you opened a Roth IRA in some past year and you never fully closed (totally withdrew all assets from it), your 5 year holding period begins Jan 1 of the year for which the contribution was made.

3. Yes. There is no limit on the number of times assets may be transferred between any IRA's, agent-to-agent. However, if the withdrawal goes directly to you to redeposit into another Roth, you have a max 60 days to do the redeposit and you may do only one of these, Roth and Traditional IRA transfers (called rollovers) per a 12 month period.

Author: IRA: A Quick Reference Guide (Amazon)
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