Basic rule of thumb for RELIABLE range at VHF/UHF frequencies is to take the square root of your antenna height above ground, in feet. That's how many miles away you 'see'. You then add the same calculation for the transmitting station, to see how far IT 'sees'. Add them together. That's your high reliability range.
It can get out to twice that, easily, at times, but only in good conditions of no hills, buildings, or foliage in the way.
Examples: Your hand held scanner: 4 feet above ground. Square root of 4 = 2. You 'see' two miles. If you were trying to hear a police officer 'direct', on his handie talkie, same for him, so, 4 miles range. (This happens to be the 'real', nevermind marketing hype, range for those GMRS/FRS bubblepack radios)
Home outside antenna at 25 feet, 5 miles.
Listening to a building/hill placed repeater at 100 feet: 10 miles.
Listening to a hill placed repeater at 2500 feet: 50 miles
These are all 'with nothing much in the way'. If there's a hill higher than you between you and the transmitter, it blocks the signal. If there's a lot of buildings or trees, same. (trees absorb UHF radio signals quite well)
Some trunk systems, usually those with a single transmitter site, have high power. Others, especially those with 5-10 transmitter sites (all same frequencies) are deliberately quite low power, and are harder to hear very far from any one of the sites.
It's a complicated question, one that cities pay a lot of money to consultants to work out in designing systems... and they STILL usually get it wrong on the first try, and have to add in sites later to cover 'dead spots'.