Bukkit

The first i would like suggest is rewrote clearly plugin (I don't know is it good idea)
The best way i would suggest by transfer people to groups is better setup settings like (1 minute, 1 hour, 1 day, 1 week

The last setting was

options:
  promoteTo: (Group to promote)
  password: password
  chatBlockEnabled: false/true
  joinMessageEnabled: false/true
  timedPromotion: false/true
  timeToPromote: (1m) (1h) (1d) (1w) or eg: 3d4m something like this.
  tickDelay: 60000
  debugMode: true

it would be really clearly to understand when player will be promoted. Also after promotion, when player reconnects (Using PermissionsBukkit) it promotes player again second time. it could be issue there. The when player also uses /apply "PASSWORD" it shows error message in console with spams multiple times then stops. Thanks for ready the ticket C:

will be my feature added C:!?

probably not, at least not on bukkit. im currently porting my plugin to the new spoutserver which should be released soon, since bukkit doesn't update further than 1.2