The asset is highly volatile and I would like to sell it while I'm transitioning in to my retirement income years. If I sold it outright, I would be paying taxes on over 90% of the value, i.e. ~923K. Taxes would amount to over $280K all in one shot. Thus the idea of moving this asset into a CRUT in the first place. But as long as I have the tax deduction, why not use it for conversions? The tax I would pay total on the conversion would still be about $215K total, but it's spread out over 4 years and then I never have to pay taxes on the Roth IRA distributions again. Of course I would then have to pay regular income tax instead of capital gains on the FlipNIMCRUT distributions after 4 years. Assuming a 5% distribution puts me in the 22% bracket (though most is taxed at 10% and 12%), plus 6.8% state.
