It sounds like you may be at the level of income where the best strategy may be tax bracket management. This is where you could look at several different scenarios of capital gains and ordinary income in different combinations to best utilize the capital gains brackets and the marginal income tax brackets. This will require a bit of time on your part.
Keep in mind that your ordinary income (like Social Security, pensions, traditional IRA distributions, Roth conversions, etc.) are taxed using the marginal rate. The long term capital gains are added to that to determine your capital gains tax rate. Any short term capital gains will be taxed at the ordinary rate.
When doing the Roth conversion consider paying the taxes from non-IRA funds. If the taxes are withheld from the converted amount, this will count as a distribution.
Charitable contributions can also lower taxable income, and when you reach 70.5 you can make a Qualified Charitable Distribution from your IRA these distributions count towards your Required Minimum Distributions (RMDs) but are not included in your AGI.
You could also speak to your broker about the advantages of selling stocks by specific identification rather than the customary first in first out method. This may help reduce your gains.
Hope this helps!
Cindy
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