With our repeaters here all being on mountaintops (and usually on tall towers above those mountaintops) I can reach about 30 repeaters, out to about 70 miles, using a 5W handheld and a whip from my patio. They do all the work. For simplex, I've experimented using just a handheld and a whip to another guy using the same thing and range is maybe 2 miles or so. If I sit on my roof (I do that sometimes) I can work the Catalina repeater with the handheld/whip and it's about 45 miles away over a somewhat obstructed path. Again, the repeaters are doing all the work. I suspect in the case of the OP, something's wrong with the setup.