I need help picking out a GPS for a middle-aged man who's not great with technology..?

The lower priced units would be best as they don't have all the "bell and whistles" the more expensive units have ie. MP3 player, bluetooth, etc. I would definitely get one with "Text to Speech" which speaks street names. Go to http://the-portable-gps.com and check out the comparison charts for the different manufactures. Garmin probably has the easiest menu. At any rate you can see all the units that offer Text to Speech. The prices listed are the MSRP and you can get them a lot cheaper than that.

Thank you for using IMshopping!  The Garmin StreetPilot C320 Portable GPS Navigator comes highly reccomended on http://www.amazon.com and is extremely user friendly. 

Features:

• Convenient touch screen allows for quick access to features such as addresses, recent locations, food, and lodging
• Features a SD card slot, a 128 MB SD card, and MapSource City Select street data on CD-ROM
• Data can be transferred from a PC to the unit via a fast USB connection
• Customize the unit's appearance with an array of colored faceplates (sold separately)
• Bright 3.5-inch diagonal, 16-bit color display