That, indeed, would be ideal but one takes what one can get. On the other hand, once the price is down 95% there is no sense in holding on to the position. It’s time to look for the next trade. Just because I was planning for the optimal trade it’s not the only possible trade. One takes what one can get. 
So rooting for the underlying to go down in order to buy back at $0.10 does not make much sense IMO, at least not if you are planning to sell the next month at the same time.
I’m not rooting for the underlying to go down in order to buy back at $0.10! But once it goes down to $0.10 it makes no sense to hold on to the position. Time to close and look for the next trade!
Not sure why the OP was posted here.
Because I chose to post it here, among Foolish Friends.
The Captain