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>Should we again convert the 2000 contribution back into a Roth in 2001?
Depends. Do you have the cash to pay the additional income tax?

> Can we?
If your modified AGI is under $100,000.

> Does it make sense?
There are plenty of calculators on the Web that will guesstimate whether a Roth or a Traditional is better. If you're in a low enough tax bracket now, I think it does.

Also, I have a small amount of money in a community retirement fund that I need to roll over into an IRA. Can I do this into a Roth and still make a $2,000 contribution?

Just make sure you do retirement fund -> Rollover (Traditional) IRA -> Convert to Roth IRA

And here's the ultimate stupid question...forgive me, I'm new at this. How many separate accounts do we need, anyway? One Roth for each of us? Do we each need a separate account?
Yep. There's no limit on how many IRAs you have.

And can I contribute $2,000 to my own account, roll my retirement savings into the same account, and requalify my traditional IRA "into" the same account as well, all in one year?
Yes, if your income allows it and you can pay the taxes.
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