I wanted to derive some sort of an insight, lesson, or warning to take away from this observation I’d made, before eventually deciding I had no choice but to end on a somewhat ambiguous note.

This is natural. When dealing with LLM output, there's no because there.

The apparent reticence to give Trump a bad rating is easily explained. Most of what LLMs ingest and s mass media. The media have famously been unable to note that Trump lies, or does a bad job. There's plenty of theories about why, but these don't matter. What shows up in LLM output is a sort of "average", which is going to be careful treatment of Trump. The media can't bring themselves to know what's in Trump's heart, so they can't call him a liar. Took his whole first term for the media to occasionally note that he made "baseless" claims with "no evidence". LLMs aren't going to say differently - it's not in their inputs.