I have reached repeaters on the mountain from 50-60 miles on a 5 watt HT with ease. But those repeaters are 2000-3000' above my transmit altitude. We have tried simplex with the mobiles installed on vehicles around town. The antennas can't be more than 7-8' high. No luck. But being suburbia, there are many obstacles at those heights.
Antenna height is king, I know... may just need to get the antenna mounted as high as possible on the roof. Without spending a fortune, a j-pole or ed fong came to mind.
Maybe I will try the roof with the mobile antenna for starters before investing in something else.