I am seeking help with an situation where I use the immediate tax deduction available from moving highly appreciated assets to a FlipNIMCRUT to convert an existing IRA to a Roth IRA. For simplicity, let's say I have an existing $1m traditional IRA and a $1m brokerage account position (with a low cost basis / high capital gain). It's my understanding that, after moving the asset to the CRUT, I can spread out the tax deduction for up to 5 years, but it's limited to 30% of AGI given its asset class. Would it make sense to move the asset to a FlipNIMCRUT that delays distributions for up to 5 years while doing a Roth IRA conversion with the tax deduction? I would live off of savings with low expenses meanwhile. Since the deduction is limited to 30% of AGI, BUT also any IRA conversion amount is considered income, how would this work, assuming $200K is converted for each of 5 years? (Let's leave out any ongoing gains/losses in the IRAs during the process for more simplicity). Does this mean I can only use 60K of the deduction each year (300K total) and would have to pay income tax out of pocket on the remaining 700K (140K per year)?
