I am sort of wondering if I should comment at all, or let you do your brainstorming regardless where it takes you

Your choice - if you want me to comment on everything, or whether you prefer to first "brainstorm" and only when you say "okay, I think
this is the answer, because..." I should respond why it's wrong
I can say this though - don't stretch it. My riddles tend to be often more straightforward than people think they are. If you saw any of my previous ones, I keep saying that every time, and yet every time people are imagining that I am a) speaking metaphorically b) about Inglor Felagund's fifteenth cousin, c) calling him a pineapple, whereas what I am talking about actually, is the pineapple Bilbo Baggins had for breakfast.
And one more thing I could tell you for sure - both the subjects of the riddle are specific, they have their own names (so not "unnamed king of Cardolan" or such).