The Garmin Hand helds will leave "tracks" to determine where you have been. My Garmin GPSMap76Csx does that well. However they lack good turn by turn directions.
For street use, i recommend a Garmin Nuvi as the street pilot series are now out of production. we got our Nuvi 750 at Sams club for $315 out the door. The thing I like is that I can also load music in it and it will broadcast to an FM station. that way both directions and favorite tunes are available.
for low $, I heard that the Tom Tom is a good unit. However I also have heard it compared that Tom Tom will get you close, Garmin will get you within 6 feet.
to date, we have the Garmin C530 Street Pilot, 750 Nuvi, and GPSMap76Csx (hiking, boating, etc.)