As long as he understands the bet he is taking,it's not a big deal. Trading an OTM conversion with less risk of being assigned will be priced accordingly.No free lunch. I don't love the bet as vol is so cheap.If he gets assigned,the residual put will be cheap.. My guess is the risk reward is 1:1
During the interim before expiration, if the price drops below the strike of the put more than the price of the call then you might get a +ve profit on the put and the call. If you think the price is going to be going up for the dividend, you might want to buy back the call in addition to selling the put but the problem with that is that the price of the stock will also be dropping and if the price of the stock drops further you won't have the put there to protect you so you will have to sell the stock at the loss at the same time when selling the put hoping that the profit on the put is larger than the loss on the stock or you can risk it with the stock to see if the price will rise later for the stock to appreciate.
Edit: Sorry I forgot to add the premium of the Call that you shorted. So your loss will be reduced to -2.28 + 1.5 = $- 0.78 in this worst scenario.
You are really complicating this. He's got a small embedded short Delta. Should the stock drop,the conversion will go his way with limited profit. Why lift the entire short leg ?? Totally different bet
To avoid the whipsaws. If the stock later on goes up close to the expiration with the short assigned (with the stock coming up it's very likely) after the stock has already been sold then he's short naked, an even worse situation imo.
Max loss if assigned is .78 minus whatever the long put sells for. What whipsaws are you talking about???
Ok I forgot the OP is long in the stock. Ok I was right then. The two mistakes are too low of call strike which increased the prob. of the assignment and too close of the expiration date of the put. Anyway...
you are guaranteed to sell your stock at $136 which you brought at $126.38 loss 38 cents o enter that position your premiums gained were a loss of 40 cents but the dividend of $1.14 means yes you make 36 cents per stock or 0.3% over the period not great but at least its risk free.