I will point out that it is likely if you sell over several/3-5 years, the tax (on gains) will be long term capital gains at 15%, which is only 3% over your 12% max, which to my mind is unimportant, although you may well disagree. So you can steadily sell 1/4-1/3 of these positions and move the proceeds into index funds over the next few years, since they also will generate capital gains at 15% tax.
Like you, I'm also..... slowly... simplifying our portfolio, mostly because we have 8 accounts and about 30 mutual funds (I got rid of 10 or 12 last year). Combining several of DW's small accounts over the last two years helped clear the way to simplifying.
My brokerage is only about 8% of our portfolio, which holds (too many) CEFs, so I also combined about 1/3 of them and switched to a US market and international index ETF, which doesn't generate much taxable dividends, just long term capital gains (see opening comment). I do take tax losses to offset gains and also try to stay below the 12% max income tax level; if I miss by a couple or 5K, though, I don't worry (haven't yet).
The E-trade IRA (DW) is only about 8%, about 2/3 in stocks. I struggle with your question, but I tend to sell half the position when it doubles, or about 1/3 when it goes up 2/3 and put the gains in an ETF or index mutual fund. At some point I will merge this E-Trade account with her (now large) Fidelity account.
Not sure this helps though, except for my point about the 15% LTCG tax is not much of a big deal if you are in the 12% bracket.
Like you, I'm also..... slowly... simplifying our portfolio, mostly because we have 8 accounts and about 30 mutual funds (I got rid of 10 or 12 last year). Combining several of DW's small accounts over the last two years helped clear the way to simplifying.
My brokerage is only about 8% of our portfolio, which holds (too many) CEFs, so I also combined about 1/3 of them and switched to a US market and international index ETF, which doesn't generate much taxable dividends, just long term capital gains (see opening comment). I do take tax losses to offset gains and also try to stay below the 12% max income tax level; if I miss by a couple or 5K, though, I don't worry (haven't yet).
The E-trade IRA (DW) is only about 8%, about 2/3 in stocks. I struggle with your question, but I tend to sell half the position when it doubles, or about 1/3 when it goes up 2/3 and put the gains in an ETF or index mutual fund. At some point I will merge this E-Trade account with her (now large) Fidelity account.
Not sure this helps though, except for my point about the 15% LTCG tax is not much of a big deal if you are in the 12% bracket.