Hey Thrass, the relevant section you need to read is in Street Magic, pg 69, second paragraph. Right after the bit that explains the threshold it says:
Note that large magical groups (such as the Illuminates of the New Dawn) are in fact associations of smaller groups, so only the local membership counts towards this threshold.
Then if you look on pg 72 of Street Magic, you can see the IOND and Jamil lslamyah membership and how it is broken down.
If the group you are trying to join is Cracking the Bones from Magical Societies, well that is a society, not a magical group. While it lists 300 members, they aren't all magical and the Magical groups within that society will be much smaller, similar to how the IOND or maybe Jamil Islamyah is broken down.
Hope that helps.