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Question 2:
My dad set me up a SIMPLE retirement account a few years back at a full service broker that is bringing in meager gains. I feel ready to manage my own account and want to move it into a discount broker Roth IRA. Are there any penalties in making this move? Things I should be aware of?

If it has been over two years since the Simple was first funded you can roll the Simple over to a Trad Ira, then you can do a Roth conversion. The original broker will likely charge you $50-100 to close the account.

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