What version of Conquest do you have. The version is at the bottom left of the initial menu screen. Are you using any mods? The critical error is the first one. The game can't generate the random loot in the chest. This is an old issue that I haven't seen for several versions.
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Latest version of the game. Used Conquest Tweaks and MGEdits. I tried a fresh install with no mods and the chests worked, so it likely has to do with one of those. All the associated files are the same as vanilla though, checked the associated lines in the corresponding gd files and they were the same. Are they trying to add loot from one of these mods and failing to generate it?