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Hi Fellow Fools,

I'm about to sell some mutual funds so I can get into the Motley 4 and am trying to decide the best way to sell the funds.

I have some shares that would qualify for long term capital gains and some that would be short term. I assumed at first that I should claim to have sold the oldest first, and thus pay taxes based on long term rates. But then I noticed that if I sold newer shares first my cost basis would be a lot higher since the NAV was a lot higher for the new shares. In this case the shares would be short term though.

My tax bite this year would actually be lower if I sell the newer shares with the higher cost basis even though they would be taxed at the short term rate.

What to do? Any clues?

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