The issue has been resolved where the server would randomly crash. Here is the backstory of what happened.
What happened was we had a plugin to help with the Mob AI to optimize the mobs and keep them from just running against a wall. The issue was that after 5-10 minutes of someone joining, it would cause the server to crash being Exception Ticking World. Due to the fact that this occured, we have removed the plugin that has caused this problem since updating to 1.16.2. Since rolling back will cause chunks to not load, it was a better idea to go ahead and remove the plugin as it hasnt been updated since September 10, 2019.