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To: JHR who wrote (5782)12/3/1998 8:56:00 PM
From: Thean  Respond to of 14427
 
JHR,
The site most useful in answering option tax question is the CBOE site.

cboe.com

Keep in mind that a lot of situations will not be illustrated and the best way to defend one's position is through an experienced CPA. One can ask several of them on the tax thread:

Subject 17266

With regards to your questions,
1) The last day to establish or sell a position is the last trading day of the year, not the settlement date.

2) I think selling different option of the same company does not qualify as "substantially different security". However, there are finer points to consider and only an expert option CPA can answer and provide strong basis to defend you against IRA. Personally, unless we are fund managers playing with millions of taxable dollars I would just pay the tax and keep IRA off me. The only difference is pay now or pay later.