My main issue with the chip damage is that it currently feels inconsistent - some attacks deal 0 damage while others deal 2-3, without much of an indication other than memorizing "oh, this skeleton has a broadsword", which just feels a bit janky. It also interacts a bit weirdly with the healing system in my opinion - if my main way of healing is by leaving party members out of fights, I feel like fights with only one enemy should let me do that without taking mandatory damage. Maybe blocked attacks could be 1 damage with clear indicator that they were blocked, and then being Safe reduces that to 0 to give you more of a reason to Buckler over just Disengaging?
As for randomization... yeah, thinking about it more my issue is less with randomization and more that the feedback I got didn't make me realize that I was just very unlucky (I swear, I missed like four Circle Formations/Engages on the same enemy in a row). Another possible suggestion would be to represent resistance to the fray/disarming by making those enemies immune to AoE abilities - in other words, Circle Formation or similar attacks would pull every melee enemy into the fray, but you'd have to use Engage on each ranged or flying enemy individually.
Thanks for the encouragement - hopefully I'll have time to get back to it this week!