The Nuvi 500 and 550 has the IPX7 waterproof rating that other Nuvi devices don't have, so it should be fine in that regard. That doesn't necessarily mean it's as rugged as other handheld/trail GPS devices. Garmin states the Li battery holds ~8hr charge. That may be fine if you just want to power on the device if/when you actually need it...or when your use allows you to recharge it as needed...or if you want to carry around extra batteries @ $40/ea.

The Dakota suggested by gpsblake sounds like one of the more user-friendly devices from Garmin. However, I don't see that $200 bundle offered anywhere. From what I see, it would be closer to $300 for the Dakota 10 with maps. That's still not particularly expensive for what you get.

FWIW, Garmin software doesn't have a great reputation for being user-friendly. There's a bit of a learning curve, and some aspects can be frustrating to the new user. Perhaps the Garmin automotive devices are highly intuitive, but the handhelds seem to require some investment of time while you get familiar with them.

I haven't used the Garmin Nuvi/Dakota/etc touchscreens, but I would get annoyed if they're like some other touchscreens that don't work well with wet, cold, sweaty or gloved fingers.

You don't state how exactly you want to use your GPS, but devices that take AA batteries are preferred among tourers and other long distance riders.

If I had a "non-techy" friend in the market, I'd suggest they take a look at the Delorme Earthmate PN series. I recall the PN-40 getting good reviews for ease of use, high quality display, and excellent preloaded maps. My Vista HCx is a good, lightweight device with fairly rugged construction, however it lacks a touchscreen and might not otherwise be what you want. The GPSMAP series would also be on my list today.