Good point Bull
However the problem is not so much on the Sell end as it is on the Buyback.
Selling, you don't care too much if the stock is forced down a bit because the loss will be written off against profits and can be carried forward to be used in future years.
To make the deal most profitable you have to be able to buy back in at close to, and preferably below, the price for which you sold your shares.
If you try to make that Buy in a single trade you may cause this thinly traded stock to jump up and away from your bid, just like the decline you warned about for a large sell.
So if the stock is thinly trading in mid-January you would buy back in in several incremental lots designed to not wake up the neighbors.
Remember too that I am anticipating the price in January to be lower than it is today which makes the ploy even more viable.
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