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I'm about to give up on my Airmap 300 and after reading all of the articles, I'm thinking that the Garmin 196 is the way to go.
Anyone have any history to share?

I have and use a 196 a lot in my 152 (and the car) and it works great. They came up with new software last year for it that added towers (an additional database for $35/update) and it works really well.

The 296 has a slightly different display design, it has color, terrain mapping, audible terrain/tower warnings that you can wire into an intercom system, and uses a rechargeable battery rather than 4-AAs like the 196. If you want to use it in the car the 296 gives you "voice" navigation (like the ads on TV show - "turn right in 1/2 mile", that kind of thing). It's twice the price of the 196 though.

We use a 396 at work and if you want to go all-out the 396 is really neat with the added weather capabilities, on-map TFR mapping, XM radio, and voice warnings (instead of a beeper you actually hear a "terrain! pull up! pull up!" type warning). We also have a Garmin transponder that adds TCAS-like traffic overlays with altitude/vectors right on the GPS display, and when someone's within a certain range of you a voice yells "traffic" in your ear.

I've been mulling over getting rid of the 196 for a 296 or 396 (the color displays are really nice for both the 152 and car), but I haven't convinced myself to spend the money.

One other comment for everyone with Garmin 196/296/396s: it's relatively easy to set up Microsoft Flight Simulator and the GPS(s) so the GPS reflects what the simulator is doing. It makes experimenting with, and learning how to operate the GPS really easy without wasting time in the airplane or using the built-in sim-mode. If anyone wants details drop me a note.