I bought my Dad a GPS 45 as a holiday gift in 1995.  Got it retail at a little electronics store in northern VA. and remember paying about $350. I guess it was one of Garmin's first small handheld models.  
In 1997 my Dad had it with him on a trip to Denver, CO for work and I was helping him.   I remember seeing the hand-held sitting there idle at the hotel, so I took it outside and marked the location as a waypoint just for kicks.  
As it turns out, a few days later, I'm by myself driving the rental Isuzu SUV; we had gone fly-fishing the day before.  I end up getting lost in some residential area off Colfax Ave. in Denver and spend a bunch of time driving around.  So, I pull over to see if I can find a city map in the vehicle.  I open the glove box and there's the GPS 45.   This was before maps or anything on handhelds, but I found the waypoint for the hotel and that provided a carrier-pigeon effect that reoriented me until I got back to surroundings near the hotel that were visually familiiar.  
Never expected that a short time later they'd have handhelds with maps like the Street Pilot.  
The first unit with Maps I bought was a GPS V that I got the tail-end of 2002 at a West Marine store for about $450.   It was WAAS-enabled.  It only had 19mb of membory -- enough to hold maps for maybe a large city.  But the thing was worth its weight in gold driving around some city I didn't know my way around like Los Angeles.  
Right now for the road though I'm using a GPS app on my BlackBerry that has traffic reports and no limits in terms of maps.  The only catch is you need a cell signal.  So I still have the GPS V around