Just wondering, what is the highest level a new team could enter the league system. I know AFC Wimbeldon started in Combined Counties Football League (which I believe is 8th division), is that the highest starting point or is there a way for a new team to enter in the Isthmian or even Conference south if they have the money?
The Combined Counties Football League is the ninth level, not the eighth level. The eighth level for clubs in that part of the country is part of the Isthmian league.
Chester FC started off in the 8th tier a few years ago (10-11), and they are already up to Conference North the 6th tier. Initially they were put in the 9th tier but an appeal got them to the 8th. http://www.thefa.com/Leagues/NewsAndFeatures/2010/chester-180610
Guernsey FC from the island of Guernsey in the channel islands. Promoted once already and set do get promoted. They are paying for the flights of their competitors to travel but i think this will finish soon.
