Carrie, Cary is a little upscale and more or less a yuppie suburb of Raleigh. Carrboro and Chapel Hill are more laid-back and granola. Chapel Hill is a college town with about 40,000 residents, half of whom are college students. Carrboro butts right up against Chapel Hill.
Living wise, I'd choose Carrboro in a heartbeat over Cary, but I understand about the commute. You don't want to be on I-40 during rush hour twice a day. Outside rush hour, though, the drive will only take about 30 minutes, so if he can be flexible on his work hours that might work just fine.
Durham also has sections that are not bad, and Ninth Street in Durham used to be a very cool, alternative street. Not sure if it still is. Durham is a city, though (400,000 inhabitants), so it also has some scary sections. Don't go live in one of those
My mother grew up in Cary and my grandparents lived there until they died, in one of the older sections (obviously
), which was therefore not at all yuppified. But then you have lots of older people, and all the house are from the 50s and early 60s.