That is a big IF. I bet they don't fill you at mid market. It is a wide market in a relaticly thinly traded option. The market is 2.00 wide!! I bet they ding you for another .25-.75 than you are planning. Are you willing to pay that?
I'm not sure getting around IRS is his goal. If it is a lock up period, I'm not sure what you are concerned about would apply. I have had a reputable IB tell me I could short some stock that was locked up in a separate account as long as I had the margin to cover. All I'm saying is there might be other reasons to do this other than tax.
There might be other reasons. But he should be aware of the potential issues. I had assumed it was tax related.
Thanks to both of you for these answers. I have a good picture now of my options (no pun!). I did not expect to receive such thorough, thoughtful answers, so thank you for your time and expertise. Jay