I am looking to sell some deep in the money calls on an existing position. What are the costs of beign assigned? Take today for instance - I could purchase some GOOG share at 378 and turn around and sell a 300 call for roughly 80 having a gain of $200 per contract, somewhat risk free. Will the assignment costs eat this up?
ask your broker what their assignment fee is....its usually a flat fee and fairly reasonable at discount on-line brokerages
Keep in mind that tying up $37800 for 2 weeks means you'll either be forgoing $72 (if you're using cash that would otherwise be getting 5% interest) or paying up to $145 (if your broker's margin rate is 10%).
You risk/reward sucks. You are risking $29,800 (37,800-8,000) per contract to make $200, which will be eaten up by commissions and cost of carry. Nothing's risk free!
If you are a customer of IB, be very careful about playing with selling in-the-money options--unless, as in the example you gave, you have the underlying stock.