Maximizing Roth Conversions in 1999?

[Guest Richard M]

Assume that you wish to convert $100K in mutual funds from Traditional IRAs to Roth IRAs in 1999. Assume also you have eight Traditional IRAs with $50K in each. Why not convert all eight mutual funds from Traditional to Roth IRAs in early 1999 and come April 15,2000 recharacterize the six mutual funds that had the least increase in value? Would not this conversion strategy maximize the value of your 1999 Roth IRA conversion while taxes would only be paid on the $100,000 of the two mutual funds that had increased the most in value prior to tax filing deadline in 2000? Your input is appreciated.