Add training workflow, datasets, and runbook

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Chapter 41: Taxes 923
able to participate in any rally in the stock in the next 30 days. If the underlying
stock has listed put options, the investor may be able to partially offset this neg­
ative effect. By selling an in-the-money put at the same time that the stock is
sold, the investor will be able to take his stock loss on the current year's taxes
and also will be able to participate in price movements on the underlying stock.
If the stock should rally, the put will decrease in price. However, if the stock ral­
lies above the striking price of the put, the investor will not make as much from the
put sale as he would have from the ownership of the stock. Still, he does realize some
profits if the stock rallies.
Conversely, if the stock falls in price, the investor will lose on the put sale. This
certainly represents a risk although no more of a risk than owning the stock did. An
additional disadvantage is that the investor who has sold a put will not receive the div­
idends, if any are paid by the underlying stock.
Once 30 days have passed, the investor can cover the put and repurchase the
underlying stock. The investor who utilizes this tactic should be careful to select a put
sale in which early assignment is minimal. Therefore, he should sell a long-term, in­
the-money put when utilizing this strategy. (He needs the in-the-money put in order
to participate heavily in the stock's movements.) Note that if stock should be put to
the investor before 30 days had passed, he would thus be forced to buy stock, and the
wash sale rule would be invoked, preventing him from taking the tax loss on the stock
at that time. He would have to postpone taking the loss until he makes a sale that
does not invoke the wash sale rule.
Finally, this strategy must be employed in a margin account, because the put
sale will be uncovered. Obviously, the money from the sale of the stock itself can be
used to collateralize the sale of the put. If the stock should drop in value, it is always
possible that additional collateral will be required for the uncovered put.
THE SHORT-SALE RULE - PUT HOLDER'S PROBLEM
A put purchase made by an investor who also owns the underlying stock may have an
effect on the holding period of the stock. If a stock holder buys a put, he would nor­
mally do so to eliminate some of the downside risk in case the stock falls in price.
However, if a put option is purchased to protect stock that is not yet held long enough
to qualify for long-term capital gains treatment, the entire holding period of the stock
is wiped out. Furthermore, the holding period for the stock will not begin again until
the put is disposed of. For example, if an investor has held XYZ for 11 months - not
quite long enough to qualify as a long-term holding - and then buys a put on XYZ,
he will wipe out the entire accrued holding period on the stock. Furthermore, when
he finally disposes of the put, the holding period for the stock must begin all over