I have studied many different versions of democracy, where claims have been made that "this time it will work" however, every single one skips over the problem of freedom of association.

In a free country, doesn't a person have the right to be involved or not? Doesn't everyone have the right to choose who they association with, and what ideas they wish to follow?

A democracy within a free market, or private sector, allows someone to walk away if they are forced to vote, or if the vote does not favour them.

For example; a club member can cancel their membership if he disagrees with a vote, or is forced to vote.

The problem you need to address, is when a persons right to associate is removed, and a vote, referendum or democracy is forced upon the individual, and they are unable to walk away.

For example; when a government forces us to vote for either government A or government B. How about no government?

You are not free when all you are given is a vote on how much exercise time you get in the prisons yard.