Suggestions

Similar to Hermes above suggest, I think you should add a cap to fight rerolls, a max of two rerolls per fight, one per player in that fight. This will help level the field for members who don’t have a large stack of items to use not feel railroaded.

Secondly, maybe a second optional fight system that requires both members to agree to use,in a sub group on the discord where they are assigned hit points based off age and health status, and they can get a certain perk based off one of their skills (less detailed perks, like fighters can add x amount to 1 attack roll per fight, healers can roll a d10 one time to get extra hp etc) and then they can use a dice bot and do short paragraphs and roll a d20 back and forth till someone’s HP hits 0. This could be used for rank challenges, spars etc. I feel this would help fights go faster and if the main fight system is kept as the primary for DM, raids etc the Fight judges won’t have as much on their plates.