IE/IWM -- How to roll down the cost basis?

I currently have 2200 shares with a cost basis of $117 per share, with IWM currently at about $112 a share.

Reading a message on another board, a question struck me -- how could I go about adjusting that cost basis downwards, keeping the $500 per week income goal, but not giving up any capital?

I fooled around with a workbook, using my add-in, and came up with the table below:

Shares	Basis	Strike	Needed	Per Share	Expiry	Bid	WriteDown	Income
2200	$117	$117	$500	$0.23	2014-06-21	$0.25	$0.00	$550.00
2200	$117	$116	$2,700	$1.23	2014-08-16	$1.46	$2,200.00	$1,012.00
2200	$117	$115	$4,900	$2.23	2014-09-20	$2.56	$4,400.00	$1,232.00
2200	$117	$114	$7,100	$3.23	2014-11-22	$4.08	$6,600.00	$2,376.00
2200	$117	$113	$9,300	$4.23	2014-11-22	$4.57	$8,800.00	$1,254.00
2200	$117	$112	$11,500	$5.23	2014-12-20	$5.57	$11,000.00	$1,254.00

Where:

• "Shares" = My current number of shares.
• "Basis" = My current cost basis.
• "Strike" = The strike price at which I want my new cost basis to be.
• "Needed" = How much is needed to generate a week's worth of income PLUS writing down the cost basis to the strike price, of the currently held shares.
• "Per Share" = What "Needed" comes down to on a per share basis.
• "Expiry" = The expiration date I'd have to use for the given strike price to generate the "Needed" amount.
• "Bid" = The bid price at the given strike price and expiration date. This should always be higher than the "Per Share" amount, because I'm actually using the "Per Share" price to look up the necessary call contract I need to use.
• "WriteDown" = How much of this call sale would go to writing down the cost basis of the currently held shares.
• "Income" = What's left over for income on the call sale after removing the write down amount.

Note that in many cases, the transaction would account for multiple weeks of income.