To simply explain my situation, I have an ESPP plan that purchases company stock once a month and I sell it as soon as I am able to since I'm not interested in holding the company stock long term. I only use the ESPP to take advantage of the company's 15% discount to (in theory) lock in a free ~15% gain.
There is usually about a week between when the shares are purchased, and when they hit my account to sell them. Going over my 1099-B this year, I see that every single sale over the entire year was a loss that effectively ate up the entire 15% discount. Despite this, the stock itself is up almost 50% over the same timeframe.
My question revolves around the timing of my sales. Am I shooting myself in the foot by immediately selling my shares? Is there a common phenomenon where so many people are doing what I'm doing that it tanks the stock value temporarily? Should I be waiting 2 or 3 weeks after they hit my account to sell?
It seems crazy to me that 12 consective monthly sales to all resulted in losses totalling a couple thousand dollars that I can't even claim yet due to wash sales while the stock saw such a positive gain over the same timeframe.