Yep it's now 5 plugins that could be merged cause each is cool and brings features the others don't.
The 2 SkirmishRaidTracker, RaidRollsn, RaidAssistant and now this one. ^^'
EDIT : I just tested it... OUCH ^^'
1 - Your settings file goes in AllServers... It has to be in ServerName\AllCharacters.
2 - Why load a Main.lua that loads a Main.lua ??
Now you have Plugins\ChallengeTracker\ChallengeTrackerMain as foldertree.
Change to Plugins\Ramble\ChallengeTracker and loads directly the good Main.lua, it'll better for everyone.
3 - Can you remove the "Adding lock for [...]" from the chat? Useless spamming.
4 - When you check the timestamp, do you care the timezone? It seems it check local, and it can be not cool.
5 - Don't understand why you write your "databases" in the settings file if you already have them in your script.
Take a look at the 2 others plugins named "SkirmishRaidTracker".
You have the potential to do my fav plugin to manage that