@Aliyah
Agreed, "experience" is difficult to define, as is skill. I suggested 500 villages as an example because at different levels of account size, the gameplay is different. Having 5, 500, or 5000 villages consists of different gameplay, a different type of experience and perspective. Yes, I know "skill" would be un-trackable in-game, which is why I said, "It'd be nice if....could...". Yeah, I can agree to the last statement. Hopefully helping the smaller players does encourage the player to grow and continue to play. We certainly need a new stream of players on this server. For far too long the player count has been going down, and the same players keep winning. It'd be awesome to see a tribe full of new players beating the older players.
@Gangnamstein
Yeah, I agree, I don't see AI being integrated into Tribal Wars. Even if Inno could, I doubt they'd do it because the benefits would not outweigh the cost to implement it.
You mentioned players that find mid/late game tedious and quit. They have limited experience as to how end-game goes. Regarding players that only play startup. They have limited experience. If they only play startup, then they can't give sound advice on long-term plans.
Extra:
If the mentoring system's only goal is to get players to 5 villages. I really am making this a bigger deal than need be.