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You don't have to sell your single stocks to start an index IRA, but Vanguard will charge you fees each year your account is under the minimums.

Vanguard charges $10 per year for each fund you hold in an IRA with an account balance below $5000. I believe money market funds are exempt.

Vanguard charges $10 per year for each index fund you hold with an account balance below $10,000.

You can rollover your stocks to Vanguard, and hold them in an IRA brokerage account there. Vanguard charges $20 to sell a stock though.
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