1) In this scenario, can I still deduct the loss for 21 shares (27 minus the 6 I purchased in the 30 day window)
yes - but was there a purchase in last March????
2) Will the 1099 account for this and will TurboTax guide me through it?
if it's all from the same broker, it should, but you are responsible for reporting it correctly on the tax return, none-the-less. Turbo Tax can handle this
3) If I had RSU vest in the same window, I would not be able to claim that number of shares as well? So say in the above scenario that I received 10 RSU shares on 5/14, then I would now only be able to deduct the loss for 11 shares (27 minus 6 purchased through ESPP minus 10 received as RSU)?
correct
