Handhelds are useless when you need a range of 300 miles. In Connecticut they won't get between two adjacent towns separated by a hill.
Often, they won't even go across town if there is a hill in the way.
100W rigs and light lithium batteries could meet your needs, assuming that you have quiet locations for installing the relatively large antennas.
Then you would need to learn the basics of propagation and ham radio protocol.
Yes, ham radio has the equivalent of "rush hour," popular contests that will clog up some amateur frequencies for a weekend.
Most drivers know they can't get quickly from here to there at certain times.
In some places it is dangerous to simply be out at night in certain parts of a big city. Not on the driving exam but "everyone knows."
