You discussed the cost basis of TNA in the OP. 900 TNA shares at $76.00 So what is the problem? Profit was $80,000 until the TNA trade - unrealized loss of $18,900 at the time of your OP. Profit now $60,000 or so. What is your macro view?
So to point out: OP has made a lot of money himself in various accounts trading covered calls. OP has a trust that has made exceptional amounts of money selling cash secured puts. Trust is now down a little bit of money and OP doesn't know what to do. OP doesn't want to discuss details of his position. How is this a real question?
You seemed to be an experience investor and have your own methodology. What I learned over the years is I could not successfully invest using others' method. So, if I were you I would exit and invest it your own way. By the way since you are already recouping, why ask the experts here? Good luck.
Here are some questions. A. Do you have the legal right to take over the trust? B. Are there other beneficiaries? If you are the trustee, then you have an obligation to them to preserve the trust's assets, not dick around with it. The trustee did well with his strategy. So there's a draw down now. Big deal. If you are the only beneficiary, and are the legal trustee, then do whatever you want to do. If not, I'd be careful and conservative, until the assets of the trust have been distributed.