I’d say, at least for me, I try to remember that “cynical” is not always correct. Under the same idea as “trust, but verify"

Isn't that already what cynicism prescribes?

Believing or showing the belief that people are motivated chiefly by base or selfish concerns; skeptical of the motives of others.

Negative or pessimistic, as from world-weariness.

Expressing jaded or scornful skepticism or negativity.

Skeptical of the integrity, sincerity, or motives of others.

It would seem, at least to me, we might not be disagreeing much but instead at a point of not quite getting our ideas across to each other, which is fair because words can have multiple meanings even within the same context.

I would say my point of contention are these 2 sentences

I extend the benefit of the doubt, but less so when there is some real risk or cost to me.

I lose little to nothing in keeping myself open to the possibility (and hope) that someone is being honest with me, while still looking for the signs that they might not be.

As to me, they seem somewhat contradictory, as the first with the benefit of the doubt seems contrary to the second with looking for the signs that they might not be worthy.