When the skip is running, it certainly is possible.
Under normal conditions, the transmitting antenna would need to be at about 2000 feet, which pretty much rules out everything except mountaintops and aircraft.
The only way that trunked and conventional systems differ is that trunked systems have centralized control over each radio's frequency - that's how they separate 'talkgroups' from 'channels'. So distance is a non-factor - a 460 mhz trunked system will talk just as far as a 460 conventional system given the same radios and repeater site.
It would be based on the number of towers and the location of the towers to your proximity. I live in flat land and can get a trunked system thats 50 miles away as good as local stuff. I believe they have a tower on the Northern end of the county which would take 20 miles off.......Hoser
The range of a system has little to do with whether it's trunked or not. But be aware, a lot of trunked systems are simulcast, multi-site systems in congested areas, and the system designers often go to great lengths to make sure a system IS NOT heard much beyond it's intended service area. This has nothing to do with scanners (they don't care one way or the other) and everything to do with co-channel users, and proper operation of the simulcast system. Bottom line is, outside of a systems service area, it's pretty hit and miss how far away it can be heard.
It could be possible depending on certain factors:
1. Frequency you are listening to. Higher freqs are more directional and travel shorter
distances. HF travel further than UHF freqs
2. Reception location/terrain. Being on a mountaintop would receive better. Some DXers
go close to the water as signal travel further over the water than land.
3. Atmosphereic conditions and seasons. Ducting, scatter would allow long distance
reception.
4. Power and mode of transmission. HF in USB at 1000watts would travel further than FM
at 1000 watts.
5. Receiving equipment/antennas used.
6. Polarization of signal.
and I'm sure there's more that I can't remember right now.