I have had a hand held GPS since 1999. My first was a Garmin GPS Pilot 3 which was excellent. I then got a 296 which was a 'giant leap for mankind'. I found the 296 to be user friendly, simple and robust. I have also used the Skymap 3 which is somewhat dated. OK but the graphics are not brilliant.
I am also lucky enough to fly a Garmin 530/430 equipped aircraft commercially and as you would expect they are awesome. Watching a hold or an ILS happening on autopilot is just great. But you really don't need the extras that the 530 provides.
Also, I am not convinced that you need to go for a 496 or a 495. The 495/6 has many features which can only be accessed in the US. The list of UK VRPs which is a major factor for buying a 496, is available on the web to download.
VFR Waypoint Add-Ons. Don't be afraid of downloading this, it is really simple. Just install the Garmin disc which comes with the 296 and follow the instructions. It is easy to delete the VRPs (in the Orkneys for example!) you don't want. The website also has all the UK DZs, glider sites, HLSs etc.
I have used a 296 for some 1000hrs now and would advise anyone to go for it, ahead of any other GPS.