Most HTs or portable radios are 5 watts, generally within a 5 mile distance between a transmitter and a repeater is workable. However the land scape, obstructions, antennas play a huge role in RF. Like in NYC if your running a 5 Watts simplex on portable your lucky if you make it up to a mile. But I hear in other places open areas, line of sight people reach 2-3 miles on simplex. So many factors play a role in RF, your best bet like others have mentioned is to experiment and see the results you get.
I remember once I was in Queens on a ems call and couldn't make it to a repeater that was less than two miles away, the landscape was basically hilly. We use UHF, all I had to do was walk 10 feet up a slope and was able to contact the dispatcher loud and clear, walked right down and lost her again. RF is very complex when it comes to reception.