@Crow Bar: UHF and VHF don’t work very well in “rolling hills” and like mentioned previously, UHF doesn’t penetrate pine trees well. What you’ll need is someone to consult with to find a high point where you can set up a cross-band repeater to cover your area of operations, and (worst case) have the ability to build directional antennas to hit it. Basically, you’ll need to have a site survey done by some local hams to see what will actually work in your area. What works for your location may not work the next valley over, and vice versa.
So you’ll need a license, so you can get hooked up with the local hams. Otherwise it’s spend an arm and a leg having a commercial shop set you up.