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Subject:  Another wash sale question Date:  9/27/2020  7:29 PM
Author:  dcy42001 Number:  131131 of 131762

It is obvious that I do not understand the "wash-sale" and "replacement shares" of trades which, in the past, I did frequently building up a considerable long term loss and deferred loss.

Also, due to reverse splits interesting things happened involving options with this stock which recently expired.

Specifically: I now have 10 shares of a stock (DUST) which my broker is carrying at:
Purchased: 6/4/2019 Price paid=421.51 Long
How can I sell this stock to generate a long term loss without triggering more "wash sales and or replacement shares"?

I am 81 years old and am now ready to throw in the towel as it seems no matter what I do, I always have lots of short term gains (to pay taxes on), and all my long term losses become "deferred"; losses which I can only take at the rate of $1500 per year. If I throw in the towel and live to 250, I might be able to use them all up.

I have also considered selling covered calls on stocks more than a year out. If they are called out at expiration, any gain would be long term since they had been held more than a year. Is that correct? If they are NOT called out, I could either sell the same covered call again, or sell the shares at whatever they were priced at expiration and generate either a long term gain or loss. Is that correct?

I am having memory problems and the rules are so confusing I cannot get a grasp on them.

I enjoy this board very much as well as a few others and wish you all well.

I thank you for any advice or help you can give an "old guy" that is starting to lose it all. The entire port is only 200-250K but retirement income, housing, and health care are not a problem for me.

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