Yes 2m is good, also 70cm band. You can get a handheld that covers both. Line of sight yes but you can also transmit to a “repeater” station that rebroadcasts your signal over a wide area depending its’ coverage. Good luck!
Looking at a topo map, he's a little lower than me and there's some knolls in between that are a little higher in elevation. Depends on how accurate these online maps are. The personal google map of repeaters is off compared to his address on google maps. Enough so that a knoll may or may not be in the way. Gonna run out there now and see if I can find a tower. It's 5 miles away.
This gives you an idea of the terrain. My location is at the higher of the bold lines in the green area and his is almost that high in the white area, depending on his tower location. I'm close to centered, just NW of little bitty knoll and he's N/NE of me in that white neighborhood looking area.
Could a repeater be powerful enough to overcome a 20-50 foot tall knoll and/or trees in between me and it if I have a low power unit(handheld or mobile) and no tower?