I agree with your financial advisor. (If it helps I used to be a financial planner, and, yep, stock broker, now retired). You would only want to "dump in" 600k of income in a year, "only in a compelling reason"..otherwise, do a little at a time. If you want or need the money, rich people borrow it, such as against your IRA. Some even borrow money and keep borrowing, never paying taxes on gains. Borrowing money does not create a taxable event. If anything, you may be able to deduct that interest. I took a chance and converted basically all my Fannie mae in IRA to Roth. I did it when the share price was much less, so now the gains are not taxable in the roth. I further suggest "tweaking" your "harvesting 100k per year gains" to do so when it suits you best. As an example if your income is otherwise low that year, then harvest more taxable gains, however, if you made a pile of money elswhere to pay tax on, then hold off and only convert a portion of your FNMA "ira to roth" conversion.
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