I often feel the same way about playing nice with the left. They've been so deranged, and so ruthless and engage in behavior that seems to exceed the normal boundaries within the depravity of politics, and seem entirely un-left-like (pre-Trump left, that is) e.g. the Kavanaugh hearings, that it's tough to maintain any level of decorum with them as a whole, let alone take them seriously. And the specific idiots here on the flip? (yeah, I'm talking about idiots like you, Little Stanley) Yeah, the gloves are about 80% off with those klowns.
Re: her specifically, I have the same negative reaction to her lying hypocritical bull$hit that you do. However, and this is just my $0.02 worth, I don't think the tranny narrative serves any useful purpose. Perhaps the contrary.
I usually believe it's just common decency to leave first ladies, or former first ladies out of the political arena, UNLESS they have entered that area voluntarily, which she certainly has done.
So savage her on the issues. Expose her lies and hypocrisy. But the tranny stuff? For me at least, it's not a productive way to attack the left. That having been said, they're not children, even though they often behave as such, so they're should be able to take it.
Oprah? I'll save my thoughts on her for another time. (brevity called, and said thank you!)