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I was intrigued by TMF Taxes idea of selling a mutual fund to create capital gains instead of ordinary income.

We have a collection of actively-managed mutual funds opened in 12/96. After taking a closer look at the expense ratios (~1.15%!), I realize that we need to eventually make a change to an index fund.

I am tempted to sell before the payout date of Dec. 1, although I am nervous about it. This is a regular brokerage account that we hope to tap until our pension plans kick in (15 years or so).
We need to choose a tax efficient vehicle for managing this nest egg until we need it.

Has anyone had success with selling out prior to payout?
What is a good rule of thumb for timing the transition from growth-oriented account to an income-producing account?
Does one typically open a single Index fund with a lump sum of money, or open a couple?

Thanks for the assistance!
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