Anyone know when American Airlines updates its fares? I know the airlines traditionally open up seats in different price classes at a certain points... any clue when that happens?

Daily. Sometimes hourly. Which fares and to what locations are you referring? They really do change constantly.

Its going to sound crazy... but I'm really just looking for a super cheap flight thats over 1000 miles before end of the year. Out of Newark (EWR). I was looking at Newark to Chicago. Had seen a fare for $160 for a while. It recently jumped to $300+, and I'm wondering if it will drop down again.

Every week, AA lists its sale routes. Since EWR isn't a AA hub, you will likely be limited to flights to Chicago, Dallas, St. Louis, maybe LA. I'd just keep watching the AA lists--I think they come out on Tues. and Weds--and just be prepared to make a last minute run.

Go to itasoftware.com and search fares. Plug in Newark as your departure airport, and then pick a city like Chicago as your destination. You can then tell the search to include all cities within 300 miles of Chicago and see what comes up. Then search Nashville, Charleston, New Orleans or wherever...and include everything within 300 miles.
American also lists weekend deals on their website, usually for leaving on Sat and coming back Monday....these change weekly.

When you see a really cheap fare, can't you put it on 24 hr hold on-line? That's what I've done in the past...that way I don't have to make a decision in two seconds.

Even if you go ahead and purchase the fare, pepper, you can cancel within 24 hours...it's a credit-card rule. The airline usually won't offer this information unless you press the issue.

Another search that you can do on ITA is a month-long search. Pick your two cities and a date, and it will show you the prices for the next 30 days after that date....so you can plan around the cheapest times if you're flexible.