What cogset do you have on the back?
In the last 5 years, I've ridden a triple (52/42/30), a standard double (53/39) and a compact double (50/39). The terrain here in Austin is mainly rolling hills with occasional steep climbs.
I'm a little confused by the description that your gears "over lap". This is normal. Each chainring provides you a range of gear options when mated with a cogset on the rear. The ranges over lap on purpose.
Below are three tables showing gearing combinations for each of the three chainring configurations, mated with a 12-27 cogset on the back.
I set these tables up to represent the MPH you'd be traveling if you were pedaling at 80 RPM. While unrealistic, this is the easiest way for me to think of how gearing affects speed...instead of gear-inches or some other measurement.
Per z90's suggestion, try riding mostly in your middle chainring. This will probably serve the bulk of your needs. When you run out of gears on the middle chainring, then it's time to move to either the bigger or smaller chainring, depending on whether you're going uphill or down.