Take a look at http://www.artscipub.com/repeaters/ and figure out if there are any amateur repeaters covering where you live. Repeaters aren't free to own and operate; if they exist it's probably because someone is using it. If there's coverage, there's hope that you'd be able to communicate with your neighbors.

FRS is not going to work for your needs. It's too limited in antennas and output power.

GMRS allows for better antennas and power, but is in my experience rarely useful beyond a couple miles, even with high-end "36 mile" radios. A sufficiently advantageous terrain feature can help out a lot. A GMRS repeater might allow for coverage that meets your needs, but that's a huge expense for you to shoulder.

You could potentially put up a big antenna for CB and perhaps get better coverage with it.

Amateur radio will definitely have the best chance to give you that "next hill" range you need...as long as you have someone to talk to with the right gear on the right frequency. Between amateur and CB, for you, it likely boils down to what the people you want to talk to are using.