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?
Repeaters are usually installed at high elevations, either towers or high terrain. Here in NW Wa (Puget Sound) they are up on mountains so they are easy to reach by handheld. I would love to live in the boonies like you :)
But I do live on an Island here (Camano) so that is kinda cool.