"TT is creating a ST loss due to only "seeing" the cash received for the transaction and not the stock."
I don't understand what you are saying here. "ST" or "LT", "Gain" or "Loss" has NOTHING to do with TurboTax only "seeing" cash received. ST and LT is set by "date acquired" vs. "date sold" and TurboTax "sees" nothing beyond the proceeds you enter, be it cash or cash + FMV of stock. The "RSU" aspect of the stock adds no additional complexity what so ever. Whether the stock was acquired five years ago through your broker or 2 days ago via an RSU changes nothing. You still have to make a lot-by-lot analysis of gain or loss, you still need to "derive" a basis to use for each lot.
If you're unsure here, start a new question that refers to the EMC/Dell deal.
