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I'm guessing u should only pay tax on 2520. everything else should be written off as capital loss or investment cost. Then again, I'm not familiar w/ us tax law.

US equity option are automatically exercised when it's at least $0.01 in the money. But what price do they use to determine if it should be used to exercise? do they use the price at 4:00pm closing or 8:00pm after market trading closing? Do they use middle of bid/ask or last traded?

I believe Caissa Capital was doing it mainly with option before they were shut down. They were mostly doing volatility arbitrage. ie play with the gap between imp vol and realized vol.