An HHR, really? Lets see how that stacks up against the competition.
I took your suggestion ADD and did do a craigslist search in your area. I found a ton of vehicles for sale that meet nearly your exact criteria. I didn't even post nearly all the cars that I found.
2007 TOYOTA PRIUS PACKAGE # 6 ... 45K ... RED ... TAN LEATHER ... 2007
2006 Toyota Prius Hybrid 5DR Hatchback Low 44k Miles Black
2005 HONDA CIVIC HYBRID - 50MPG - BLUE - 52K MILES - AUTO-SEDAN
This one is a steal:
2010 HONDA INSIGHT HYBRID Low Miles
2005 Toyota Prius
2006 Toyota Prius Liftback, Traction Control, Push Start Button, #4010
2006 Toyota Prius Hybrid◄-QUALITY SELECTION!@Select Motors
2005 Toyota Prius-Very practical Hybrid!!Free service contract??
As for the maintenance of hybrids, the Prius has one of the lowest costs to own of any vehicle out there. If you're really worried about things shy away from the Honda hybrids as they tend to have a few more issues (though most are easily fixable if you know what you're doing).