Yes the repeaters tend to travel further because they are often 250w - 1000w, versus the HT and mobile rigs that are between 1 and 50w.
I am sure your concerns are being addressed by those in the county. There is a huge aversion to digital almost everywhere, in the scanner communities, in the public service communities, in the ham communities. I don't understand it, necessarily, but it certainly exists.
In a conventional VHF system the HT's usually run 5 w, mobiles 100 w.
When you get into many trunking systems the HT's are downgraded to 1w and mobiles to 50w because IN THEORY there are more satellite receivers around your coverage area than in a conventional system thus less wattage is needed by the users in the field.
The trouble with drop outs in a trunking system isn't the repeaters------its in the mobiles and their line of sight(and distance) with the receive antenna's of the systme
The aversion to digital in the public service community is driven by the fact that the radio is the "lifeline" for the officer in the field.
Conventional mobile 2 way ----you push the button and talk...........base hears you if you are in range. When it works there is no middle man to get in the way.
Trunking mobile 2 way-----you push the button.............a computer someplace decides if you are important enough to override the user already on the frequency or other factors. There is an extra step in the process that could (and many times does) go wrong. The benefits usually outweigh the downsides and Trunking seems to be much more accepted that it used to be by the end user.
DIGITAL Trunking mobile 2 way adds another step in the process..........actually 2 steps that can go wrong . The digitizing of the signal in the field and the decoding at the base. This is where most public safety officers are resistant. Another computer is in between the officer and potential help.
As more and more systems are in use the benefits will win out in the long run.....................and the officers will learn to trust the system.
Cops don't like change...................they don't trust their lives on new stuff until they understand it works.