Failed to run a 0.50 timer in 'LoadingMessages v1.0.7' (NullReferenceException: Object reference not set to an instance of an object)
  at Oxide.Plugins.LoadingMessages.HandleString (System.String raw, System.String playerName, System.Boolean isQueue, System.Int32 ahead, System.Int32 behind) [0x00041] in <8c27b8e14fc849b9b9dd7527d990e13a>:0

  at Oxide.Plugins.LoadingMessages.DisplayMessage (Network.Connection con, Oxide.Plugins.LoadingMessages+MsgEntry msgEntry) [0x0005e] in <8c27b8e14fc849b9b9dd7527d990e13a>:0

  at Oxide.Plugins.LoadingMessages.HandleClients () [0x0007e] in <8c27b8e14fc849b9b9dd7527d990e13a>:0

  at Oxide.Core.Libraries.Timer+TimerInstance.FireCallback () [0x00018] in <50629aa0e75d4126b345d8d9d64da28d>:0

__________________________________________________________________________________________________________________________

Failed to call hook 'OnUserApprove' on plugin 'LoadingMessages v1.0.7' (NullReferenceException: Object reference not set to an instance of an object)
  at Oxide.Plugins.LoadingMessages.HandleString (System.String raw, System.String playerName, System.Boolean isQueue, System.Int32 ahead, System.Int32 behind) [0x00041] in <8c27b8e14fc849b9b9dd7527d990e13a>:0

  at Oxide.Plugins.LoadingMessages.DisplayMessage (Network.Connection con, Oxide.Plugins.LoadingMessages+MsgEntry msgEntry) [0x0005e] in <8c27b8e14fc849b9b9dd7527d990e13a>:0

  at Oxide.Plugins.LoadingMessages.OnUserApprove (Network.Connection connection) [0x0004a] in <8c27b8e14fc849b9b9dd7527d990e13a>:0

  at Oxide.Plugins.LoadingMessages.DirectCallHook (System.String name, System.Object& ret, System.Object[] args) [0x000b0] in <8c27b8e14fc849b9b9dd7527d990e13a>:0

  at Oxide.Plugins.CSharpPlugin.InvokeMethod (Oxide.Core.Plugins.HookMethod method, System.Object[] args) [0x00079] in <e23ba2c0f246426296d81c842cbda3af>:0

  at Oxide.Core.Plugins.CSPlugin.OnCallHook (System.String name, System.Object[] args) [0x000d8] in <50629aa0e75d4126b345d8d9d64da28d>:0

  at Oxide.Core.Plugins.Plugin.CallHook (System.String hook, System.Object[] args) [0x00060] in <50629aa0e75d4126b345d8d9d64da28d>:0

I am just wondering if this is potentially an issue or I have caused this issue myself. I can provide Config file if needed.

Yeah, show me your config please.

{
"Text Display Frequency (Seconds)": 0.5,
"Enable Messages Cyclicity": true,
"Use Random Cyclicity (Instead of sequential)": false,
"Cycle Messages Every ~N Seconds": 4.0,
"Messages": [
{
"Top Status": "<color=#0099ff>ISL.GG One-Grid!</color>",
"Bottom Status": "<color=white>Global T1 Workbench!</color><color=#0077ff><br>Discord.gg/QhcdDTsTqX</color>"
},
{
"Top Status": "<color=#0099ff>Balanced Loot+!</color>",
"Bottom Status": "<color=white>Link your account extra perks!</color><color=#0077ff><br>link.islggservers.net</color>"
},
{
"Top Status": "<color=#0099ff>Daily Challenges!</color>",
"Bottom Status": "<color=white>Type /Pass</color>"
},
{
"Top Status": "<color=white>With</color> <color=#0099ff>Launchsite</color>"
}
],
"Enable Queue Messages": false,
"Queue Messages": [
{
"Top Status": "<color=red>You're in queue...</color>",
"Bottom Status": "<color=#add8e6>{AHEAD} got in before you.</color>"
},
{
"Top Status": "<color=#add8e6>I guess you really like this server!</color>",
"Bottom Status": "<color=#ffff00>{BEHIND} players followed you here.</color>"
}
],
"QueuePosition": null,
"Last Message (When entering game)": {
"Top Status": "<color=#ffff00>Going in!</color>",
"Bottom Status": "<color=#0099ff>Play nice...or dont.</color>"
}
}

Could it be due to not having a "bottom status" on the last non-queue message?

Ill retry adding the bottom status and just leaving the "" blank. If so, sorry for wasting your time for my user error xD

Could it be due to not having a "bottom status" on the last message?

Most likely.

Disregard. Apologies for wasting your time. User error on my behalf.

I took out bottom message to see if It would always display loading info, vs the bottom message.