How much do you have in total with him and what are your all-in expenses?
Are your married? How long until you’re ready for retirement and potentially having an income below $101,200? Beginning in 2018, if your adjusted gross income is below $77,200 and you are married, your rate on capital gains will be 0%. (You can earn $101,200 in total because the standard deduction is $24,000 now).
I have plenty of stocks I want to part with and just put the money in an index fund, but I’m less than two years away from having a 0% capital gains rate and have been selective in which ones I’m choosing to sell now. I have to expect them to underperform the market by more than 20% over the next two years to make it worth selling.