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yogibearbull
Valued Contributor

Double-up by Nov 29, Sell Old Lot by Yearend & Other Tax Strategies

There are many tax strategies if one has underwater positions. To paraphrase former Chicago Mayor RIE, don't let a loss [or crisis, in the original version] go to waste.

One strategy is to sell the position at loss and buy something similar but not identical right away. Options won't do as they are considered too similar. But another fund or industry stock would be fine. Selling a R2000 index fund and buying another R2000 index fund may be just cutting it too close [don't try to fool Mother Nature or the IRS].

Another strategy is to double-up on a losing position now and sell the old lot by the yearend. Deadline to do this is Nov 29 this year. That is Black Friday on which the stock market closes early at 1 PM Eastern. Get this out of the way before shop-until-drop.

The idea behind the above is to avoid wash-sales.

If one has a highly appreciated stock or fund, consider funding donor advised fund [DAF] with it. One will escape the CG tax and also get a tax deduction on itemization. One can manage the DAF, dole out grants gradually, but that money is out of one's estate.

 

 

YBB
2 Replies
yogibearbull
Valued Contributor

Re: Double-up by Nov 29, Sell Old Lot by Yearend & Other Tax Strategies

Bumping up as this OP will sort of expire on Fri, Nov 29 at 1pm Eastern.

YBB
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ctyankee
Explorer ○○○

Re: Double-up by Nov 29, Sell Old Lot by Yearend & Other Tax Strategies

Yogi,

Excellent strategy, as long as you want to keep the stock ongoing.  

ctyankee

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