A (not well thought out) Thought Experiment ...

[Bluenorthwest]

36. Not nearly enough information to answer. As it stands, the most important bit of information is that

one group has fortified and holds high ground. Why have they done those things? Castle suggests warfare and need for major defense. From what or from whom and why? What is the source of their wealth, how do they produce far more with far fewer hands? If they are a few people holed up in a castle, where is their food coming from, who is providing their labor?

There is so little here that I would suggest it might be better if you just clearly made the point you wish to make. This set up you offer is sketchier than the lyrics to One Tin Soldier.

But as it stands, I'd be off to negotiate with the people that the castle dwellers fear, for I have no castle, am not protected by those on the hill and thus can not afford enemies. Perhaps for lack of a castle, I must build my defenses upon alliances, it seems the hill people are indifferent to alliance and thus of no value to me at all. If assisting their enemies might serve me, then perhaps I would do that. They do seem short handed, paranoid and expecting trouble.