I've been told that the portable Garmin and TomTom models were the most user friendly out of the box vs. Magellan.
Depending on the manufacturer, user manuals are available online and are a great source for help judging what extras you want or don't want to pay for.
I just ordered a portable Garmin Street Pilot C340 online yesterday that is arriving today in anticipation for a trip to Philadelphia on Saturday. There are some excellent deals online vs buying it locally. Got the jump by reading the manual online and it had to been one of the most painless manuals I've ever had to go through.
Garmin C340 manual
And for about $100 less, the C330 model does everything the C340 does except for Traffic Alerts via subscription and the identifying of the upcoming turns with actual street
names in the voice overlay.