As to your first question, it depends. Need some clarification regarding the "ISO same day sale." Does this mean that the incentive stock option was exercised (purchased) and then sold on the same day. If yes, then it appears the RSU loss would be a wash sale. The wash sale covers the period 30 days before the sale and 30 days after the sale. The starting point for wash sales is with the sale that results in a loss. Thus, we start with the sale of your RSUs which were sold at a loss. Was this loss allowed or disallowed per the wash sale rule? In your scenario, the RSU shares were sold at a loss; however, four days earlier, ISO shares were purchased. The ISO purchase happened within 30 days of the RSU sale. Thus, the wash sale rule is triggered.
As to your second question, yes, because when RSUs vest, that is the equivalent of a purchase. Because the RSUs were sold for a loss, the subsequent purchase--four days later--of the same security through the exercise of the ISO triggered the wash sale rule. You are correct in that the loss gets added to the cost basis of the ISO shares. And yes, the RSU loss is disallowed.
@bluecloud33
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