I was in an employee stock purchase program that auto-bought stock every two weeks at a 15% discount as part of a paycheck deduction. This was BEFORE the 2008 crash and during and after it. This stock started at, say, 100, and was being bought every two weeks for a two year period. It would go to 90, 80, 70, 60, down to 10 for several paycheck periods, then back up to 20, bought for those types of fluctuated prices, and now it's up to 20 and stayed this way for years. I'm giving you a rough idea of how it fluctuated over two years because I'd like some advice on how best to sell it and report the sales to the IRS. I have a spreadsheet of the number shares, the date bought and the price paid. Now I want to start selling it.
For example, one option is to sell some of the stocks once a year for the next 3-4 years and claim a 3K tax loss each time - so my income would be lowered each year.
Another option is simply to sell it all and claim the 3K loss and carry it to next year.
I want at least some of the cash for a down payment. I'm not really sure what strategy to follow, especially since I recently read a NY Times article that said that the rules changed in 2013.