"Guild master 4 different times for 4 different guilds? This whole thing is a really epic idea but this part doesn't make any sense to me...."
I forgot to mention that you can be a guild master for only a certain period of time. This is to keep the cycle going, so that no one will get stuck being an apprentice for the rest of his life. So that way to you can hold a guil master office for 4 times. This does sound crazy, but the rewards you get once u accomplish it is even more crazier... so it ill be worth it. :P
Starting a guild is never too early. Its a very long process to get to know one and another once there are a few members... honestly I wihs i could have started much earlier.