I want to know, when do you think we will break away from this 2 party system?
Yes, we have made some small progress in recent elections, (Perot '92 and '96, Ventura in '99, Johnson '12 and '16, McMullin 2016, and as of now, 1 Independent Governor and 2 Senators.) but we have not truly seen the system break permanently for a third option to stay in the competition.
So like I said, my question is... when? When will the system be more fair to third parties? When will they win?
When you change the constitution to abolish the presidency and/or introduce a PR component to the electoral system for legistlatures. Until then, it could only happen temporarily, in a transition to a new two-party system.