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My current income would place me in the 0% long-term capital gains bracket currently, while I anticipate them to be 15% within my working years that commence in 2018.

My stocks (an index fund) have appreciated about 50% since I bought them (most of these should be capital gains).

Wash sale rules would probably prevent me from investing in the stocks for 30 days, which means I'm expected to lose out on <1% growth.

If I anticipate liquidating the stocks before retirement (in my working years), shouldn't I go ahead and do a sell-rebuy in order to make the next cost basis larger (which reduces the next long-term capital gains on the next sale)?

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Wash sale negates, or rather, delays, losses. Gains? You can sell/buy at the same time, take the gain. Uncle Sam won't object.

When you say index fund, I trust you mean a mutual fund. You should be able to find one nearly identical to the one you have, and buy/sell at the days close. You won't miss a day in the market.

This might also be a good time to consider a Roth conversion with some IRA money. Just a thought.

  • Regarding your second comment, I really want to stay in VTSAX. I might sell to money market in one day, and then buy in again on the next day. I need to confirm that I won't end up in a higher bracket with the sale. Regarding your third comment, I only have a taxable account, so there's nothing I can really convert from I believe. – Wuschelbeutel Kartoffelhuhn Jul 3 '17 at 9:42
  • I understand. It's perfectly fine. For the reader who feels "with my luck, the market will choose to go up 2% the day I am out," I suggest just buying a similar fund. Stay with Vanguard, grab the VTSMX, the higher fee .15 vs .04 will cost .01% if the holding period is a forced 30 days (I don't recall if Vanguard has a min holding time). The .01% is far less that the 'reader's' perceived risk of 2%. Back to you - consider opening a Roth IRA this year. – JTP - Apologise to Monica Jul 3 '17 at 12:19
  • The cycling of admiral to non-admiral back to the admiral is a great idea. I just have to make sure that it's a taxable event from admiral to non-admiral first. I know it wasn't a taxable event when I did the reverse years ago. – Wuschelbeutel Kartoffelhuhn Jul 3 '17 at 12:51
  • Let us know. That may be true, in which case the lesser favored choice is to go the their S&P 500 only, just for short period. Either way, you have some choices ahead of you. – JTP - Apologise to Monica Jul 3 '17 at 12:56

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