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Besides seeing an estate planner who should be able to look at a variety of options, you should look at the overall investment according to how you think they will appreciate in the future and selective sell the least promising one.

Taxes also will be capital gains which will help. Be careful to seek advice of a tax expert so that the AMT does not claim too much of the sell off.

Now is the time to look at alternative investments to increase returns but from what I see, your grandmother needs to be getting 10% return on $1 million to cover the $50,000/yr care and $50,000 for gifts. The only way to get this return is long term growth equity investment which will require a risk to the principle.

I would certainly recommend dollar cost averaging in moving money into new investments. A 5 year plan may work.

Just look at some of the numbers. You need to determine the dividend yield on the investments and
the taxes paid to estimate the time needed to make up for taxes using a more aggressive strategy.

And you are correct in trying to help your grandmother find a bit more aggressive returns.

BGP
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