1. Under each credit line there is a little section that says "High Balance:" is this just the highest reported balance ever on a certain credit card? It doesn't effect my utilization right?
That's right. It generally doesn't get taken into account.
2. the "Recent Balance:" is what I am assuming is supposed to be the thing thing that is directly tied to my utilization.
Again, absolutely correct.
3. How long does it usually take Discover and Chase to report my new limit?
Typically, they'll report the new limit after they cut your first statement that has that limit in effect. Two months at the outside.
4. Is it weird that Discover has not reported to Experian since 01/2013? AMEX, Chase, and Wells Fargo have last reported on 2/2013.
Not necessarily. A lot of things can affect if and when a card reports. It doesn't matter when the most recent report was, really; it matters that it has reported as open, and has never reported as closed or delinquent.